Method for synthesizing 2-(3-dimethylamino-2-hydroxy) propoxybenzaldehyde as intermediate of sarpogrelate hydrochloride

A technology of sagrelate hydrochloride and propoxybenzaldehyde, which is applied in the field of synthesis of 2-propoxybenzaldehyde, an intermediate of sarcogrelate hydrochloride, can solve problems such as difficulty in control, increased cost, cumbersome process, etc., and prevent palladium Effects of carbon catalyst poisoning, guaranteed recycling, and simplified synthesis steps

Inactive Publication Date: 2019-05-31
ANHUI HERYI CHEM
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  • Abstract
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  • Claims
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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 cumber...

Method used

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  • Method for synthesizing 2-(3-dimethylamino-2-hydroxy) propoxybenzaldehyde as intermediate of sarpogrelate hydrochloride
  • Method for synthesizing 2-(3-dimethylamino-2-hydroxy) propoxybenzaldehyde as intermediate of sarpogrelate hydrochloride
  • Method for synthesizing 2-(3-dimethylamino-2-hydroxy) propoxybenzaldehyde as intermediate of sarpogrelate hydrochloride

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Embodiment 1

[0023] 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%.

[0024] 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, leave to separate and separate to obtain an oil layer, wash twice with water, and anhydrous After drying over magnesium sulfate, a yellow-brown oily liquid was obtained, and 155 g of 2-(3-dimethylamino-2-hydroxy)propoxybenzaldehyde was obtained with a purity of 92.3% and a yield of 86%.

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Abstract

The invention discloses a method for synthesizing 2-(3-dimethylamino-2-hydroxy) propoxybenzaldehyde as an intermediate of sarpogrelate hydrochloride, and relates to the technical field of pharmaceutical organic synthesis.Salicylaldehyde is used as a raw material, the salicylaldehyde and epichlorohydrin are subjected to etherification reaction in the presence of a deacid reagent to generate theintermediate 2-(ethylene oxide-2-methoxy) benzaldehyde,and then the intermediate 2-(ethylene oxide-2-methoxy) benzaldehydeis aminated with dimethylamine to generate 2-(3-dimethylamino-2-hydroxy) propoxybenzaldehyde.According to the method for synthesizing the 2-(3-dimethylamino-2-hydroxy) propoxybenzaldehyde as the intermediate of the sarpogrelate hydrochloride,2-(3-dimethylamino-2-hydroxy) propoxybenzaldehyde is prepared by two steps with the salicylaldehyde, no additional reaction solvent is added, the input cost of the reaction solvent is reduced, and the pollution to the environment caused bythe direct discharge of the reaction solvent or the increased energy consumption input of the recovery of the reaction solvent is avoided.

Description

Technical field: [0001] The invention relates 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: [0002] 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. [0003] At present, there are many routes for the synthesis of sargrelate hydrochloride, including the following synthetic routes: [0004] [0005] The route first utilizes o-benzyloxybenzyl diethyl phosphite 2 and m-methoxybenzaldehyde 3 to react to generate an alkene intermediate, and then uses palladium carbon catalyst for hydrogenation reduction and deprotection to ...

Claims

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Application Information

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IPC IPC(8): C07C213/04C07C217/36C07D303/23C07D301/28
CPCC07C213/02C07D303/22C07C213/08C07C217/32
Inventor 董来山
Owner ANHUI HERYI CHEM
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