CN114436803B - Preparation method of 3- (4-chlorophenyl) -1, 5-diphenylpentane-1, 5-dione compound - Google Patents
Preparation method of 3- (4-chlorophenyl) -1, 5-diphenylpentane-1, 5-dione compound Download PDFInfo
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- CN114436803B CN114436803B CN202011184601.4A CN202011184601A CN114436803B CN 114436803 B CN114436803 B CN 114436803B CN 202011184601 A CN202011184601 A CN 202011184601A CN 114436803 B CN114436803 B CN 114436803B
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- chlorophenyl
- diphenylpentane
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- 238000002360 preparation method Methods 0.000 title claims abstract description 15
- -1 3- (4-chlorophenyl) -1, 5-diphenylpentane-1, 5-dione compound Chemical class 0.000 title claims abstract description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims abstract description 24
- 239000003054 catalyst Substances 0.000 claims abstract description 18
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims abstract description 16
- XYSHVVOXHFAUOV-UHFFFAOYSA-N 3-(4-chlorophenyl)-1,5-diphenylpentane-1,5-dione Chemical compound C1=CC(Cl)=CC=C1C(CC(=O)C=1C=CC=CC=1)CC(=O)C1=CC=CC=C1 XYSHVVOXHFAUOV-UHFFFAOYSA-N 0.000 claims abstract description 15
- 238000006243 chemical reaction Methods 0.000 claims abstract description 15
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 claims abstract description 14
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000002904 solvent Substances 0.000 claims abstract description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 10
- PTHGDVCPCZKZKR-UHFFFAOYSA-N (4-chlorophenyl)methanol Chemical compound OCC1=CC=C(Cl)C=C1 PTHGDVCPCZKZKR-UHFFFAOYSA-N 0.000 claims abstract description 7
- 238000010992 reflux Methods 0.000 claims abstract description 7
- 239000007787 solid Substances 0.000 claims abstract description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 5
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims abstract description 5
- 238000005406 washing Methods 0.000 claims abstract description 5
- 238000001035 drying Methods 0.000 claims abstract description 4
- 238000001914 filtration Methods 0.000 claims abstract description 4
- 238000000746 purification Methods 0.000 claims abstract description 4
- 238000003756 stirring Methods 0.000 claims abstract description 4
- 229960002089 ferrous chloride Drugs 0.000 claims abstract description 3
- NMCUIPGRVMDVDB-UHFFFAOYSA-L iron dichloride Chemical compound Cl[Fe]Cl NMCUIPGRVMDVDB-UHFFFAOYSA-L 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 6
- 230000015572 biosynthetic process Effects 0.000 claims description 6
- 238000003786 synthesis reaction Methods 0.000 claims description 6
- 239000008096 xylene Substances 0.000 claims description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 4
- 238000004440 column chromatography Methods 0.000 claims description 3
- 239000003208 petroleum Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000000543 intermediate Substances 0.000 abstract description 5
- 230000002194 synthesizing effect Effects 0.000 abstract description 5
- 239000003814 drug Substances 0.000 abstract description 4
- 229940079593 drug Drugs 0.000 abstract description 3
- 238000009776 industrial production Methods 0.000 abstract description 2
- 239000000126 substance Substances 0.000 abstract 1
- 230000000694 effects Effects 0.000 description 3
- 150000004698 iron complex Chemical class 0.000 description 3
- 238000006555 catalytic reaction Methods 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 150000003230 pyrimidines Chemical class 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000001914 calming effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000012450 pharmaceutical intermediate Substances 0.000 description 1
- LDIJKUBTLZTFRG-UHFFFAOYSA-N pyrazolo[1,5-a]pyrimidine Chemical class N1=CC=CN2N=CC=C21 LDIJKUBTLZTFRG-UHFFFAOYSA-N 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 238000009333 weeding Methods 0.000 description 1
- HUNXMJYCHXQEGX-UHFFFAOYSA-N zaleplon Chemical compound CCN(C(C)=O)C1=CC=CC(C=2N3N=CC(=C3N=CC=2)C#N)=C1 HUNXMJYCHXQEGX-UHFFFAOYSA-N 0.000 description 1
- 229960004010 zaleplon Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
- B01J31/1805—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing nitrogen
- B01J31/181—Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine
- B01J31/1815—Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine with more than one complexing nitrogen atom, e.g. bipyridyl, 2-aminopyridine
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/40—Substitution reactions at carbon centres, e.g. C-C or C-X, i.e. carbon-hetero atom, cross-coupling, C-H activation or ring-opening reactions
- B01J2231/42—Catalytic cross-coupling, i.e. connection of previously not connected C-atoms or C- and X-atoms without rearrangement
- B01J2231/4205—C-C cross-coupling, e.g. metal catalyzed or Friedel-Crafts type
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/02—Compositional aspects of complexes used, e.g. polynuclearity
- B01J2531/0238—Complexes comprising multidentate ligands, i.e. more than 2 ionic or coordinative bonds from the central metal to the ligand, the latter having at least two donor atoms, e.g. N, O, S, P
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/84—Metals of the iron group
- B01J2531/842—Iron
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
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- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Abstract
A 3- (4-chlorophenyl) -1, 5-diphenylpentane-1, 5-dione compound having the chemical structural formula:
Description
Technical Field
The invention belongs to the field of synthesis of pharmaceutical intermediates, and relates to a preparation method of a 3- (4-chlorophenyl) -1, 5-diphenylpentane-1, 5-dione compound.
Background
Pyrazolo [1, 5-alpha ] pyrimidine compounds are heterocyclic compounds with high activity, have the effects of resisting tumor, sterilizing, calming and resisting cardiovascular diseases, and have the effects of weeding, disinsection and the like in the pesticide field. Therefore, pyrazolo [1,5-a ] pyrimidine compounds have become a research hotspot for medicine and agrochemical.
The compound 3- (4-chlorophenyl) -1, 5-diphenyl pentane-1, 5-dione is an important intermediate for synthesizing pyrazolo [1, 5-alpha ] pyrimidine compounds zaleplon and other medicines, and most of the synthesis of the intermediate adopts expensive raw materials, has more severe reaction conditions or low yield, is not friendly to the environment, and greatly limits the industrial application of the intermediate. Therefore, it is necessary to develop a synthetic method which is easy to obtain raw materials, mild in reaction conditions and simple and convenient to operate. The invention reports a novel synthesis method of 3- (4-chlorophenyl) -1, 5-diphenyl pentane-1, 5-dione.
Disclosure of Invention
The invention aims to provide a method for synthesizing 3- (4-chlorophenyl) -1, 5-diphenylpentane-1, 5-dione by catalysis, which has the advantages of simple operation, mild reaction, low cost and high yield.
The reaction formula for synthesizing the 3- (4-chlorophenyl) -1, 5-diphenyl pentane-1, 5-dione compound by catalyzing the iron metal complex is as follows:
the preparation method comprises the following steps:
A. preparation of iron Metal Complex catalyst 4 '-chlorophenyl-2, 2':6',2' -terpyridine (10 mmol) was dissolved in tetrahydrofuran (20 mL) at room temperature and FeCl was added under nitrogen 2 (10 mmol), stirred overnight, filtered to give a solid which was washed with tetrahydrofuran and dried to give the iron metal complex catalyst.
B. Synthesizing 3- (4-chlorophenyl) -1, 5-diphenyl pentane-1, 5-dione, dissolving the iron metal complex catalyst and potassium tert-butoxide in a solvent at room temperature, adding 4-chlorobenzyl alcohol and acetophenone, then carrying out reflux reaction, removing the solvent after the reaction is finished, and purifying to obtain the 3- (4-chlorophenyl) -1, 5-diphenyl pentane-1, 5-dione.
The feeding mole ratio of the iron metal complex catalyst, the 4-chlorobenzyl alcohol and the acetophenone in the step B is 1 (30-55): 50.
The solvent in step B may be xylene, tetrahydrofuran, N-dimethylformamide, of which xylene is preferred.
The purification in the step B can be separated by column chromatography or directly washed by petroleum ether.
And (C) refluxing for 12-24h in the step (B).
The reaction of step B is carried out in air.
The invention has the beneficial effects that: 3- (4-chlorophenyl) -1, 5-diphenyl pentane-1, 5-dione is synthesized by iron complex catalysis. The preparation method is simple, low in price, high in yield, capable of performing mass synthesis and suitable for industrial production and application. The application is wide, and can be used for preparing various drug intermediates.
Detailed Description
Hereinafter, preferred examples of the invention will be described in detail. The examples are presented for better illustration of the invention and are not intended to be limiting. Insubstantial modifications and adaptations of the embodiments in accordance with the summary of the invention remain within the scope of the invention.
A process for the preparation of a 3- (4-chlorophenyl) -1, 5-diphenylpentane-1, 5-dione compound comprising: an iron metal complex catalyst was prepared by dissolving 4 '-chlorophenyl-2, 2':6',2' -terpyridine (10 mmol) in tetrahydrofuran (20 mL) and adding FeCl under nitrogen 2 (10 mmol) stirring overnight, filtering to obtain solid, washing with tetrahydrofuran, drying to obtain Fe metal complex catalyst, and catalyzing with the catalyst to obtain 3- (4-chlorophenyl) -1, 5-diphenyl pentane-1, 5-dione.
The invention will be further illustrated with reference to specific examples.
The iron complex catalyst in the embodiment of the invention is catalyzed to obtain 3- (4-chlorophenyl) -1, 5-diphenyl pentane-1, 5-dione, and the reaction formula is as follows:
example 1: preparation of iron complex catalysts
4 '-chlorophenyl-2, 2':6',2' -terpyridine (10 mmol) was dissolved in tetrahydrofuran (20 mL) at room temperature, and anhydrous ferrous chloride (10 mmol) was added under nitrogen. And stirring the mixed solution overnight, filtering, washing the obtained solid with tetrahydrofuran for three times, and drying to obtain the iron metal complex catalyst. Yield: 87.3%.
Example 2: synthesis of 3- (4-chlorophenyl) -1, 5-diphenylpentane-1, 5-dione
Iron metal complex catalyst (2 mmol,0.941 g) and potassium tert-butoxide (10 mmol,1.12 g) were dissolved in 30mL of xylene at room temperature, 4-chlorobenzyl alcohol (110 mmol,15.62 g) and acetophenone (100 mmol,12 g) were added, followed by reflux reaction for 24h, after the reaction was completed, cooled to room temperature, and the solvent was removed. Separating the obtained mixture by column chromatography to obtain the pure product, namely 3- (4-chlorophenyl) -1, 5-diphenylpentane-1, 5-dione. Yield 91.2%, characterization data: 1 H NMR (400 MHz, CDCl 3 ) ,ppm,δ :7.95 (d, J =7.6 Hz, 4 H), 7.56-7.53 (M, 2 H), 7.45-7.43 (m, 4 H), 7.28-7.24 (m, 4 H), 4.08 (J = 7.0 Hz, 1 H), 3.48 (dd, J = 6.9 Hz, 2 H), 3.32 (dd, J =7.3 Hz, 2 H); 13 C NMR (100 MHz, CDCl 3 ) ,ppm,δ: 198.2, 142.3, 136.8, 133.2,132.4, 129.0,128.9, 128.72, 128.6, 44.7, 36.5.
example 3: synthesis of 3- (4-chlorophenyl) -1, 5-diphenylpentane-1, 5-dione
Iron metal complex catalyst (2 mmol,0.941 g) and potassium tert-butoxide (10 mmol,1.12 g) were dissolved in 30mL of xylene at room temperature, 4-chlorobenzyl alcohol (60 mmol,8.52 g) and acetophenone (100 mmol,12 g) were added, followed by reflux reaction for 24h, after the reaction was completed, cooled to room temperature, and the solvent was removed. The resulting mixture was directly washed with petroleum ether to give 3- (4-chlorophenyl) -1, 5-diphenylpentane-1, 5-dione. Yield 89.5%, characterization data: 1 H NMR (400 MHz, CDCl 3 ) ,ppm,δ :7.95 (d, J =7.6 Hz, 4 H), 7.56-7.53 (M, 2 H), 7.45-7.43 (m, 4 H), 7.28-7.24 (m, 4 H), 4.08 (J = 7.0 Hz, 1 H), 3.48 (dd, J = 6.9 Hz, 2 H), 3.32 (dd, J =7.3 Hz, 2 H); 13 C NMR (100 MHz, CDCl 3 ) ,ppm,δ: 198.2, 142.3, 136.8, 133.2,132.4, 129.0,128.9, 128.72, 128.6, 44.7, 36.5.。
Claims (6)
1. a process for the preparation of a 3- (4-chlorophenyl) -1, 5-diphenylpentane-1, 5-dione compound, characterized by comprising the steps of:
A. preparation of iron metal complex catalyst: under the condition of room temperature, dissolving 4 '-chlorophenyl-2, 2':6',2' -terpyridine in tetrahydrofuran, adding anhydrous ferrous chloride under the protection of nitrogen, stirring, filtering, washing the obtained solid with tetrahydrofuran, drying, and collecting the solid to obtain an iron metal complex catalyst;
B. synthesis of 3- (4-chlorophenyl) -1, 5-diphenylpentane-1, 5-dione: the iron metal complex catalyst and the potassium tert-butoxide are dissolved in a solvent at room temperature, then 4-chlorobenzyl alcohol and acetophenone are added, reflux reaction is carried out, the solvent is removed, and the 3- (4-chlorophenyl) -1, 5-diphenyl pentane-1, 5-dione is obtained after purification.
2. The process for preparing a 3- (4-chlorophenyl) -1, 5-diphenylpentane-1, 5-dione compound according to claim 1, wherein the iron metal complex catalyst, 4-chlorobenzyl alcohol and acetophenone are fed in a molar ratio of 1 (30-55): 50 in step B.
3. The method for preparing 3- (4-chlorophenyl) -1, 5-diphenylpentane-1, 5-dione compound according to claim 1, wherein the solvent in step B is one or more selected from the group consisting of xylene, tetrahydrofuran, and N, N-dimethylformamide.
4. The process for the preparation of a 3- (4-chlorophenyl) -1, 5-diphenylpentane-1, 5-dione compound according to claim 1, wherein the solvent in step B is xylene.
5. A process for the preparation of a 3- (4-chlorophenyl) -1, 5-diphenylpentane-1, 5-dione compound according to claim 1, wherein the purification in step B is column chromatography or petroleum ether washing.
6. The process for the preparation of a 3- (4-chlorophenyl) -1, 5-diphenylpentane-1, 5-dione compound according to claim 1, wherein the reflux reaction in step B is carried out for a period of 12 to 24 hours.
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| CN202011184601.4A CN114436803B (en) | 2020-10-30 | 2020-10-30 | Preparation method of 3- (4-chlorophenyl) -1, 5-diphenylpentane-1, 5-dione compound |
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| CN106905125A (en) * | 2017-02-22 | 2017-06-30 | 荆楚理工学院 | A kind of method that ketone α alkyl of cobalt catalysis is combined to ketones derivant |
| CN107540660A (en) * | 2017-09-18 | 2018-01-05 | 东莞理工学院 | It is a kind of using terpyridyl derivative as the iron complex and its synthetic method of part and application |
| CN110423190A (en) * | 2019-07-19 | 2019-11-08 | 荆楚理工学院 | A kind of method of iron complex catalysis ketone alpha-alkyl |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN109867701B (en) * | 2017-12-01 | 2021-07-20 | 中国科学院大连化学物理研究所 | Pyridyl bridged bistriazine metal complex and preparation and application thereof |
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| CN106905125A (en) * | 2017-02-22 | 2017-06-30 | 荆楚理工学院 | A kind of method that ketone α alkyl of cobalt catalysis is combined to ketones derivant |
| CN107540660A (en) * | 2017-09-18 | 2018-01-05 | 东莞理工学院 | It is a kind of using terpyridyl derivative as the iron complex and its synthetic method of part and application |
| CN110423190A (en) * | 2019-07-19 | 2019-11-08 | 荆楚理工学院 | A kind of method of iron complex catalysis ketone alpha-alkyl |
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