Preparation process for key intermediate 1-(4-methoxyl)benzyl-1,2,3,4,5,6,7,8-octahydro isoquinoline (mixed isomer) of dextromethorphan hydrobromide serving as cough relieving medicine

A technology of octahydroisoquinoline and hydrobromic acid, which is applied in organic chemistry and other fields, and can solve the problems of low utilization rate and high cost
CN102219737BActive Publication Date: 2012-12-12JIANGSU BAOZONG & BAODA PHARMACHEM
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Patent Information

Authority / Receiving Office
CN · China
Patent Type
Patents(China)
Current Assignee / Owner
JIANGSU BAOZONG & BAODA PHARMACHEM
Publication Date
2012-12-12

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Abstract

The invention discloses a preparation process for a key intermediate 1-(4-methoxyl)benzyl-1,2,3,4,5,6,7,8-octahydro isoquinoline (mixed isomer) of dextromethorphan hydrobromide serving as a cough relieving medicine, which comprises the following steps of: performing acylation reaction to obtain 1-(4-methoxyl)benzyl-2-alkylacyl-1,2,3,4,5,6,7,8-octahydro isoquinoline (laevo isomer); and racemizing under the alkaline condition to obtain 1-(4-methoxyl)benzyl-2-alkylacyl-1,2,3,4,5,6,7,8-octahydro isoquinoline (mixed isomer); and hydrolyzing under the alkaline condition to obtain the 1-(4-methoxyl)benzyl-1,2,3,4,5,6,7,8-octahydro isoquinoline (mixed isomer). The process aims to overcome the defect of the synthetic process and reduce cost, so that the process is simply and safely operated, the industrial production is qualified, and the yield of products is between 55 and 69 percent.
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Description

technical field

[0001] The invention relates to a new process for the preparation of antitussive drugs, in particular to the key intermediate 1-(4-methoxy)benzyl-1,2,3,4, A new process for the preparation of 5,6,7,8-octahydroisoquinoline (heteromorph). Background technique

[0002] Dextromethorphan hydrobromide, also known as dextromethorphan hydrobromide, chemically named 3-methoxy-17-methyl-9α, 13α, 14α morphinan hydrobromide hydrate, is a central Antitussives mainly inhibit the cough center of the medulla medulla and exert their effects. Colds, acute and chronic bronchitis, pharyngitis, bronchial asthma, tuberculosis and other upper respiratory tract infections caused by less phlegm cough.

[0003] At present, the key intermediate of dextromethorphan hydrobromide is 1-(4-methoxy)benzyl-1,2,3,4,5,6,7,8-octahydroisoquinoline (heteromorph) In the utilization process of this step, the general yield is only about 50%. The 1-(4-methoxy)benzyl-1,2,3,4,5,6,7,8 obtained in the ...

Claims

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