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Method adopting micro-flow field reactor to prepare dimethylamino ethyl ginkgolide B

A technology of dimethylaminoethyl and dimethylaminoethyl chloride, applied in the field of medicine, can solve the problems of incapable of continuous preparation, low conversion rate of raw materials, long reaction time and the like

Active Publication Date: 2016-10-19
JIANGSU CAREFREE PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The technical problem to be solved by the present invention is to propose a method for the preparation of dimethylformamide at the shortcoming of long reaction time in the synthesis process of derivatives of ginkgolide B at the present stage, low raw material conversion rate, high reaction cost and inability to continuously prepare Method for Aminoethyl Ginkgolide B

Method used

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  • Method adopting micro-flow field reactor to prepare dimethylamino ethyl ginkgolide B

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Effect test

Embodiment 1

[0020] Dissolve dimethylaminoethyl chloride ethane hydrochloride and potassium iodide in the mixed solution of acetonitrile and water (the volume ratio of acetonitrile and water is 10%), then pump the acetonitrile solution of ginkgolide B and the above mixture into the In the fixed-bed microchannel modular reaction device of potassium carbonate, the mol ratio of ginkgolide B and dimethylaminoethyl chloride ethyl chloride hydrochloride is 1:1, and the mol ratio of potassium iodide and ginkgolide B is 0.2:1, The molar ratio of potassium carbonate to ginkgolide B is 2:1, the reaction residence time is kept for 4min, and the reaction is carried out at 70°C, the crude product is filtered, the filtrate is concentrated, and the obtained solid is recrystallized with methanol to obtain dimethylaminoethyl Ginkgolide B, the yield was 75%.

Embodiment 2

[0022] Dissolve dimethylaminoethyl chloride ethane hydrochloride and potassium iodide in the mixed solution of tetrahydrofuran and water (the volume ratio of tetrahydrofuran and water is 10%), then pump the tetrahydrofuran solution of ginkgolide B and the above mixture into the In the fixed-bed microchannel modular reaction device of cesium carbonate, the mol ratio of ginkgolide B and dimethylaminoethyl chloride ethyl chloride hydrochloride is 1:1, and the mol ratio of potassium iodide and ginkgolide B is 0.2:1, The molar ratio of cesium carbonate to ginkgolide B is 2:1, the reaction residence time is kept for 4min, and the reaction is carried out at 70°C, the crude product is filtered, the filtrate is concentrated, and the obtained solid is recrystallized with methanol to obtain dimethylaminoethyl Ginkgolide B, the yield was 71%.

Embodiment 3

[0024] Dissolve dimethylaminoethyl chloride hydrochloride and sodium iodide in a mixture of acetone and water (the volume ratio of acetone and water is 10%), then pump the acetone solution of ginkgolide B and the above mixture into In the fixed-bed microchannel modular reaction device that is filled with cesium carbonate, the mol ratio of ginkgolide B and dimethylaminoethyl chloride ethane hydrochloride is 1:1, and the mol ratio of sodium iodide and ginkgolide B is 0.2:1, the molar ratio of cesium carbonate to ginkgolide B is 2:1, keep the reaction residence time for 5min, react at 70°C, filter the crude product, concentrate the filtrate, and recrystallize the obtained solid with methanol to obtain dimethyl Aminoethyl ginkgolide B, the yield was 73%.

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Abstract

The invention discloses a method of preparing dimethylamino ethyl ginkgolide B. The method comprises the following steps: dissolving dimethylamino chloroethane hydrochloride and metal iodides into a mixed solution of an organic solvent and water, then pumping the mixture and an organic solvent containing ginkgolide B into a fixed bed micro-channel modularized reactor filled with inorganic alkali, maintaining a reaction retention time of 2 to 12 minutes, carrying out reactions at a temperature of 65 to 95 DEG C, filtering the coarse product, concentrating the filtrate, and recrystallizing the obtained solids by methanol so as to obtain dimethylamino ethyl ginkgolide B. The provided preparation method has the advantages that the whole process is continuous, the preparation technology is easy to operate and control, the reaction retention time is short, the product quality is stable, the conversion rate is high; moreover, the production devices are simple, are easy to disassemble and assemble, and are portable; by simply increasing or reducing the number of micro-channels, the adjustment can be performed easily, and no amplification effect in industrial production has been found.

Description

technical field [0001] The invention relates to a synthesis process for a class of compounds, in particular to a synthesis process for derivatives of ginkgolide B, and belongs to the technical field of medicine. Background technique [0002] Ischemic cardiovascular and cerebrovascular diseases are major diseases with high morbidity and mortality. At present, the most effective treatment is anti-platelet aggregation. However, such drugs are prone to bleeding, and the development of new anti-platelet aggregation drugs that can avoid the risk of bleeding is currently a global research hotspot. As one of the only surviving old tree species of the genus Ginkgo in the Ginkgo family, the leaves and fruits of the Ginkgo tree have important medicinal value. The most studied is Ginkgo biloba extract, which mainly includes flavonoids and ginkgolides. Ginkgolides mainly include ginkgolides A, B, C, J and M monomers, and ginkgolides A and B have a significant effect on the treatment of...

Claims

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Application Information

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IPC IPC(8): C07D493/22
Inventor 郭凯秦引林苏梅欧阳平凯伍贤志金秋
Owner JIANGSU CAREFREE PHARM CO LTD
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