An Improved Synthesis of Amantadine Hydrochloride

被引：16

作者：

Duong Binh Vu ^{[1
]}

Thinh Van Nguyen ^{[1
]}

Son Trung Le ^{[1
]}

Chau Dinh Phan ^{[2
]}

机构：

[1] Vietnam Mil Med Univ, Phuc La Ward, 160 Phung Hung Str, Hanoi, Vietnam

[2] Hanoi Univ Sci & Technol, Sch Chem Engn, Bach Khoa Ward, Bach Khoa Ward, 1 Dai Co Viet Str, Hanoi, Vietnam

来源：

ORGANIC PROCESS RESEARCH & DEVELOPMENT | 2017年 / 21卷 / 11期

关键词：

GRIGNARD-REAGENTS; PRIMARY AMINES; ELECTROPHILIC AMINATION; O-SULFONYLOXIME;

D O I：

10.1021/acs.oprd.7b00242

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Amantadine hydrochloride 1 is an antiviral drug used in the prevention and treatment of influenza A infections. It has also been used for alleviating early symptoms of Parkinson's disease. Several methods for the preparation of 1 have been reported. These procedures started with adamantane 2 using as many as four reaction steps to produce amantadine hydrochloride with overall yields ranging from 45% to 58%. In this article, we describe a two-step procedure for the synthesis of 1 from 2 via N-(1-adamantyl)acetamide 4 with an improved overall yield of 67%. The procedure was also optimized to reduce the use of toxic solvents and reagents, rendering it more environment-friendly. The procedure can be considered as suitable for largescale production of amantadine hydrochloride. The structure of amantadine hydrochloride was confirmed by H-1 NMR, C-13 NMR, IR, and MS.

引用

页码：1758 / 1760

页数：3

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