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Synthetic method of sarpogrelate hydrochloride intermediate 2-(3-dimethylamino-2-hydroxy) propoxybenzaldehyde

A technology for sarpogrelate hydrochloride and propoxybenzaldehyde, which is applied in the field of synthesis of 2-propoxybenzaldehyde, an intermediate of sarpogrelate hydrochloride, can solve the problems of increased cost, difficult control, complicated process, etc. Effects of carbon catalyst poisoning, reduced input cost, simplified synthesis steps

Pending Publication Date: 2022-04-26
ANHUI HERYI CHEM
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In order to reduce costs, it is necessary to control the residual phosphorus in olefin intermediates by recycling palladium-carbon catalysts, which is cumbersome and increases costs.
From the perspective of the whole technology, the route is long, the process is complicated and difficult to control, and the cost is high

Method used

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  • Synthetic method of sarpogrelate hydrochloride intermediate 2-(3-dimethylamino-2-hydroxy) propoxybenzaldehyde
  • Synthetic method of sarpogrelate hydrochloride intermediate 2-(3-dimethylamino-2-hydroxy) propoxybenzaldehyde
  • Synthetic method of sarpogrelate hydrochloride intermediate 2-(3-dimethylamino-2-hydroxy) propoxybenzaldehyde

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Embodiment 1

[0025] Put 150g epichlorohydrin into 100g salicylaldehyde, stir, put 120g anhydrous potassium carbonate under nitrogen protection, heat up to 80±2°C, react for 5h, recover epichlorohydrin under reduced pressure, pour the residual liquid into 300mL ice water, The organic layer was separated to obtain 143g of intermediate with a yield of 98% and a purity of 96%.

[0026] Under the protection of nitrogen, put 143g of the intermediate into 429g of 30% dimethylamine aqueous solution, stir and react at 25±2°C for 12h, after the reaction is completed, adjust the pH to 7 with dilute hydrochloric acid, stand and separate to obtain an oil layer, wash twice with water, anhydrous sulfuric acid Dried over magnesium to obtain a yellow-brown oily liquid and 155 g of 2-(3-dimethylamino-2-hydroxy)propoxybenzaldehyde with a purity of 92.3% and a yield of 86%.

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Abstract

The invention belongs to the technical field of organic synthesis of medicines, and particularly relates to a synthetic method of sarpogrelate hydrochloride intermediate 2-(3-dimethylamino-2-hydroxyl) propoxy benzaldehyde, which comprises the following steps: by taking salicylaldehyde as a raw material, carrying out etherification reaction on the salicylaldehyde and epoxy chloropropane in the presence of an acid-binding agent to generate intermediate 2-(oxirane-2-methoxy) benzaldehyde; carrying out amination reaction on the 2-(3-dimethylamino-2-hydroxy) propoxy benzaldehyde and dimethylamine to generate 2-(3-dimethylamino-2-hydroxy) propoxy benzaldehyde; the epichlorohydrin is used as a reaction solvent at the same time; no additional reaction solvent is added in the etherification reaction and the amination reaction. The 2-(3-dimethylamino-2-hydroxyl) propoxybenzaldehyde is prepared from salicylaldehyde through two-step reaction, no additional reaction solvent is added, the cost of the reaction solvent is reduced, and meanwhile, environmental pollution caused by direct discharge of the reaction solvent or energy consumption input increased by recovery of the reaction solvent is avoided.

Description

[0001] The application date is March 18, 2019, the application number is 201910212040.5, and the invention name is "Synthetic method of sagrelate hydrochloride intermediate 2-(3-dimethylamino-2-hydroxyl) propoxybenzaldehyde" divisional application. technical field [0002] The invention belongs to the technical field of organic synthesis of medicines, in particular to a method for synthesizing 2-(3-dimethylamino-2-hydroxyl) propoxybenzaldehyde, an intermediate of sarcogrelate hydrochloride. Background technique [0003] Sargrel hydrochloride, the chemical name is succinic acid mono[2-(dimethylamino)-1-[[2-[2-(3-methoxyphenyl)ethyl]phenoxy]methyl] Ethyl] ester hydrochloride is a 5-HT2 receptor antagonist and platelet aggregation antagonist developed by Tanabe Mitsubishi Pharmaceutical Co., Ltd. in Japan. It is clinically used for chronic thrombosis. [0004] At present, there are many routes for the synthesis of sargrelate hydrochloride, including the following synthetic rou...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C213/02C07C217/32C07C213/08
CPCC07C213/02C07D303/22C07C213/08C07C217/32
Inventor 董来山
Owner ANHUI HERYI CHEM
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