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Method for synthesizing evodiamine by carbonylation reaction three-step method

A technology of carbonylation reaction and evodiamine, which is applied in the fields of cell biology, clinical and medicine, can solve the problems of low reaction efficiency and cumbersome reaction steps, and achieve the effect of simple operation process, concise synthesis steps and mild reaction conditions

Active Publication Date: 2018-01-26
蛮力蛮广州医药科技有限公司
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  • Abstract
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  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are mainly four traditional synthesis methods of evodiamine, all of which use N-methylanthranilic acid as the reaction raw material, and N-methyl anthranilic acid needs to be prepared by methylation with anthranilic acid as the reaction raw material; Therefore, traditional synthetic methods often have cumbersome reaction steps and low reaction efficiency.

Method used

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  • Method for synthesizing evodiamine by carbonylation reaction three-step method
  • Method for synthesizing evodiamine by carbonylation reaction three-step method
  • Method for synthesizing evodiamine by carbonylation reaction three-step method

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Experimental program
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Effect test

Embodiment 1

[0021] (1) Add 0.2 mmol of N,N-dimethylaniline, 0.01 mmol of palladium chloride, 0.2 mmol of copper acetate into a 25 mL test tube, add toluene (PhMe) and N,N-dimethylformamide (DMF) 3 ml as a mixed solvent with a volume ratio of 10:1, covered with a balloon containing carbon monoxide and oxygen (volume ratio: 1:1) as a carbonyl source, and stirred at 100°C for 5 hours. After TLC (thin layer chromatography) detection, the reaction solution was cooled to room temperature, the balloon was removed, and the unreacted carbon monoxide and oxygen were slowly vented. The reaction solution was filtered, the filtrate was evaporated under reduced pressure to remove the solvent, and then separated and purified by column chromatography to obtain N-methyl isatoic anhydride with a yield of 27%.

[0022] (2) Add 1.0 mmol of N-methylisatoic anhydride and 1.0 mmol of tryptamine in a 25 mL round bottom flask, add acetonitrile as a reaction solvent, and stir for 8 hours at room temperature. TLC ...

Embodiment 2

[0035] (1) In a 25 mL test tube, add 0.2 mmol of N,N-dimethylaniline, 0.01 mmol of bistriphenylphosphine palladium dichloride, 0.2 mmol of copper acetate, add toluene (PhMe) and N,N -Dimethylformamide (DMF) 3ml was used as a mixed solvent with a volume ratio of 10:1, covered with a balloon containing carbon monoxide and oxygen (volume ratio: 1:1) as a carbonyl source, and stirred at 100°C. After TLC (thin layer chromatography) detection, the reaction solution was cooled to room temperature, the balloon was removed, and the unreacted carbon monoxide and oxygen were slowly vented. The reaction solution was filtered, and the filtrate was evaporated under reduced pressure to remove the solvent, and then separated and purified by column chromatography to obtain N-methyl isatoic anhydride with a yield of 49%.

[0036] Step (2) and step (3) are the same as embodiment 1.

Embodiment 3

[0038] (1) Add 0.2 mmol of N,N-dimethylaniline, 0.01 mmol of dichlorodiacetonitrile palladium, 0.2 mmol of copper acetate into a 25 mL test tube, add toluene (PhMe) and N,N-dimethyl 3 ml of formamide (DMF) was used as a mixed solvent with a volume ratio of 10:1, a balloon containing carbon monoxide and oxygen (volume ratio: 1:1) was used as a carbonyl source, and stirred at 100°C. After TLC (thin layer chromatography) detection, the reaction solution was cooled to room temperature, the balloon was removed, and the unreacted carbon monoxide and oxygen were slowly vented. The reaction solution was filtered, and the filtrate was evaporated under reduced pressure to remove the solvent, and then separated and purified by column chromatography to obtain N-methyl isatoic anhydride with a yield of 68%.

[0039] Step (2) and step (3) are the same as embodiment 1.

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Abstract

The invention discloses a method for synthesizing evodiamine by a carbonylation reaction three-step method. The method comprises that N, N-dimethylaniline as a reaction material undergoes an oxidativecarbonylation reaction to produce N-methylisatoic anhydride, the N-methylisatoic anhydride undergoes an aminolysis reaction to produce N-(2-indolylethyl)-2-(methylamino)benzamide and the N-(2-indolylethyl)-2-(methylamino)benzamide undergoes a cyclization reaction to produce an evodiamine compound. The method is a novel synthesis method, utilizes simple and easily available reaction raw materials,has simple synthesis processes, is carried out under mild reaction conditions, is easy to operate, satisfies the development requirements of green chemistry, and successfully synthesizes the evodiamine.

Description

technical field [0001] The invention belongs to the technical fields of medicine, clinic, cell biology and the like, and specifically relates to a method for synthesizing evodiamine by a three-step carbonylation reaction. Background technique [0002] Evodia rutaecarpa belongs to the Rutaceae plant and is a traditional Chinese medicine, which was first recorded in "Shen Nong's Materia Medica", and its clinical application has a history of hundreds of years. Evodiamine is one of the active ingredients of Evodia rutaecarpa, which has the functions of dissipating heat and relieving pain, invigorating the spleen and stopping vomiting, helping yang and stopping diarrhea, regulating body temperature, and losing weight. There are mainly four traditional synthesis methods of evodiamine, all of which use N-methylanthranilic acid as the reaction raw material, and N-methyl anthranilic acid needs to be prepared by methylation with anthranilic acid as the reaction raw material; Therefor...

Claims

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Application Information

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IPC IPC(8): C07D471/14
Inventor 及方华王守才
Owner 蛮力蛮广州医药科技有限公司
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