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Preparation method of dexmedetomidine hydrochloride

A technology of dexmedetomidine hydrochloride and dexmedetomidine, which is applied in the field of drug synthesis, can solve problems such as high equipment requirements, dangerous operation, and unsuitability for industrial production, and achieve simple routes, easy control of reaction conditions, and product separation The effect of easy purification

Inactive Publication Date: 2020-06-09
BOSEN BIO PHARMA SHANXI PROVINCE
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  • Abstract
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  • Claims
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Problems solved by technology

The third is to react 2,3-dimethylbenzoyl chloride with 1-N,N-dimethylsulfonyl-2-(tert-butyldimethylsilyl) imidazole to obtain an intermediate which is hydrolyzed in hydrochloric acid and Reaction of methyllithium and reduction with lithium ammonia at -78 ° C to obtain medetomidine; this synthesis method is dangerous to operate, requires high equipment, and is not suitable for industrial production

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  • Preparation method of dexmedetomidine hydrochloride
  • Preparation method of dexmedetomidine hydrochloride
  • Preparation method of dexmedetomidine hydrochloride

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preparation example Construction

[0026] see figure 1 , figure 2 and image 3 , a preparation method of dexmedetomidine hydrochloride, comprising the following steps:

[0027] 1) Friedel-Crafts reaction of 1-(1-chloroethyl)-2,3-dimethylbenzene and N-TMS imidazole under the action of Lewis acid to generate medetomidine;

[0028] 2) using L-(+)-tartaric acid to resolve medetomidine to obtain medetomidine in the dextrorotatory configuration;

[0029] 3) Dexmedetomidine is salified in hydrochloric acid solution to obtain the crude product of dexmedetomidine hydrochloride;

[0030] 4) The crude product is refined through recrystallization to obtain dexmedetomidine hydrochloride.

[0031] The first step reaction: Friedel-Crafts reaction between 1-(1-chloroethyl)-2,3-dimethylbenzene and N-TMS imidazole to prepare intermediate 1 medetomidine.

[0032] Second-step reaction: medetomidine is salted with L-(+)-tartaric acid to prepare dexmedetomidine.

[0033] The third reaction step: dexmedetomidine hydrochloride ...

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Abstract

The invention discloses a preparation method of dexmedetomidine hydrochloride. The preparation method comprises the following steps: in a reaction solvent dichloromethane, carrying out a Friedel-Crafts reaction on 1-(1-chloroethyl)-2,3-dimethylbenzene and N-TMS imidazole under the action of lewis acid titanium tetrachloride to generate medetomidine; in a reaction solvent ethanol, resolving medetomidine by using L-(+)-tartaric acid to obtain medetomidine with a dextrorotation configuration; in a reaction solvent ethyl acetate, salifying dexmedetomidine in a hydrochloric acid solution to obtaina crude dexmedetomidine hydrochloride product; and finally, carrying out refining in a recrystallization mode to obtain a finished dexmedetomidine hydrochloride product. The preparation method has fewsteps, is simple and convenient to operate and is suitable for industrial production.

Description

technical field [0001] The invention belongs to the field of drug synthesis, in particular to a preparation method of dexmedetomidine hydrochloride. Background technique [0002] Dexmedetomidine hydrochloride is a new type of highly selective α2-adrenergic receptor agonist with sedative effect, mainly suitable for sedation during tracheal intubation and mechanical ventilation in surgical patients undergoing general anesthesia, and during intensive care Begin intubation and sedation of the patient on the ventilator. As a highly selective α2-adrenoceptor agonist, dexmedetomidine hydrochloride has a ratio of α1-adrenergic receptors of about 1600:1, which is about 8-fold, which may allow relatively high doses for sedation and analgesia without unwanted vascular effects due to activation of α1 receptors. Dexmedetomidine is a short-term drug with a sedative counterpart, atipamezole. These characteristics make dexmedetomidine suitable for sedation and analgesia throughout the pe...

Claims

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Application Information

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IPC IPC(8): C07D233/58
CPCC07B57/00C07B2200/07C07D233/58
Inventor 杨慧卿王伟郭瑜李莉
Owner BOSEN BIO PHARMA SHANXI PROVINCE
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