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Preparation method of 5H-dibenzo[a,d]cycloheptatriene-5-one

A technology of cycloheptatriene and diphenyl, applied in the field of pharmaceutical synthesis, can solve the problems of low yield, high production cost, complicated operation and the like, and achieves the effects of fast reaction rate, easy operation and shortened process route

Pending Publication Date: 2022-01-14
LUNAN PHARMA GROUP CORPORATION
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0018] In summary, the current preparation methods of 5H-dibenzo[a,d]cycloheptatrien-5-one have many deficiencies in terms of process safety, cumbersome operation, low yield, and high production cost. Therefore, research to find A reaction route suitable for the industrialized production of 5H-dibenzo[a,d]cycloheptatrien-5-one with simple operation process, high product yield, high purity and low production cost is still a problem to be solved at present

Method used

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Embodiment 1

[0047] At room temperature, 3-(2-benzoylphenyl)acrylic acid (25.23g, 0.1mol), AgNO 3 (3.40g, 0.02mol), K 2 S 2 o 8 (108.12g, 0.4mol) and acetonitrile (250ml) were added to the reactor, placed in a microwave reaction device, refluxed under temperature control, and the microwave radiation power was 400W. After the reaction was completed, the reaction solution was cooled to room temperature, filtered, and the filtrate was saturated with An aqueous solution of sodium bicarbonate (500ml) was extracted with dichloromethane (250ml×3), the organic layer was dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated to dryness under reduced pressure to obtain the target product with a yield of 97.5% and a purity of 99.89%.

Embodiment 2

[0049] At room temperature, 3-(2-benzoylphenyl)acrylic acid (25.23g, 0.1mol), AgNO 3 (0.85g, 0.005mol), Na 2 S 2 o 8 (95.24g, 0.4mol) and dimethyl sulfoxide (250ml) were added to the reactor, placed in a microwave reaction device, the temperature was controlled at 115-120°C, and the microwave radiation power was 400W until the reaction was over, and the reaction solution was cooled to At room temperature, filter, add the filtrate to saturated aqueous sodium bicarbonate solution (500ml), extract with dichloromethane (250ml×3), dry the organic layer over anhydrous sodium sulfate, filter, and concentrate the filtrate to dryness under reduced pressure to obtain the target product, with a yield of 92.5 %, purity 99.76%.

Embodiment 3

[0051] At room temperature, 3-(2-benzoylphenyl)acrylic acid (25.23g, 0.1mol), AgNO 3 (0.68g, 0.004mol), (NH 4 ) 2 S 2 o 8 (91.28g, 0.4mol) and dimethyl sulfoxide (250ml) were added to the reactor, placed in a microwave reaction device, the temperature was controlled at 115-120°C, and the microwave radiation power was 400W until the reaction was completed, and the reaction solution was cooled to Room temperature, filtered, the filtrate was added to saturated aqueous sodium bicarbonate (500ml), extracted with dichloromethane (250ml×3), the organic layer was dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated to dryness under reduced pressure to obtain the target product, with a yield of 90.2 %, purity 99.72%.

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Abstract

The invention belongs to the technical field of drug synthesis, and provides a novel preparation method of 5H-dibenzo[a,d]cycloheptatriene-5-one. According to the invention, 3-(2-benzoylphenyl)acrylic acid is used as a starting material, and intramolecular decarboxylation coupling is performed under the action of a silver catalyst and an oxidizing agent to prepare a target product. The method has the characteristics of simplicity and convenience in operation, no need for isolating water and air, mild reaction conditions, high reaction rate and the like, and the product obtained by the method is relatively high in yield and purity and is more suitable for industrial production.

Description

technical field [0001] The invention belongs to the technical field of medicine synthesis, and in particular relates to a preparation method of cyclobenzaprine intermediate 5H-dibenzo[a,d]cycloheptatrien-5-one. Background technique [0002] Cyclobenzaprine hydrochloride (cyclobenzaprine hydrochloride), the chemical name is 5-(3-dimethylaminopropylene) dibenzo [a, d] cycloheptene hydrochloride, is a muscle relaxant developed by Merck Company of the United States. It is now on the market in many countries, with the trade name Flexeril, which is clinically used to relieve muscle spasm and the accompanying severe pain of skeletal muscles. This product has fast onset of action, good antispasmodic effect, and less adverse reactions. It is the first choice drug for this kind of pain. The chemical structural formula is: [0003] [0004] 专利US3454643A、387CHE2005、171MUM2011、WO2012098563A2、CN102942489A、CN103242170B及文献Acta.Chemical Scandinavica,17(1963)2437-2443、Journal ofMedicinal...

Claims

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Application Information

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IPC IPC(8): C07C45/67C07C49/675B01J19/00
CPCC07C45/676B01J19/0093C07C49/675
Inventor 张贵民鲍广龙张乃华刘忠
Owner LUNAN PHARMA GROUP CORPORATION
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