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Simple Two-step Procedure for the Synthesis of Memantine Hydrochloride from 1,3-Dimethyl-adamantane.

ABSTRACT: Memantine hydrochloride is a medicine used for the treatment of Alzheimer's disease. A number of methods for the preparation of memantine hydrochloride have been reported. These procedures started from 1,3-dimethyl-adamantane by as many as using three or four reaction steps to produce memantine hydrochloride with overall yields ranging from 54 to 77%. In this article, a simple, concise two-step synthesis of memantine hydrochloride from 1,3-dimethyl-adamantane via N-formamido-3,5-dimethyl-adamantane with an improved overall yield of 83% was developed. In step 1, 3,5-dimethyl-adamantane was reacted with formamide and nitric acid to afford 1-formamido-3,5-dimethyl-adamantane in 98% yield, followed by hydrolysis of 1-formamido-3,5-dimethyl-adamantane with aq hydrochloride to give memantine hydrochloride in 85% yield. The procedure can be easily deployed at an industrial scale.

SUBMITTER: Vu BD

PROVIDER: S-EPMC7346261 | biostudies-literature | 2020 Jul

REPOSITORIES: biostudies-literature

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Simple Two-step Procedure for the Synthesis of Memantine Hydrochloride from 1,3-Dimethyl-adamantane.

Vu Binh Duong BD Ho Ba Ngoc Minh NM Pham Van Hien VH Phan Dinh Chau DC

ACS omega 20200625 26

Memantine hydrochloride is a medicine used for the treatment of Alzheimer's disease. A number of methods for the preparation of memantine hydrochloride have been reported. These procedures started from 1,3-dimethyl-adamantane by as many as using three or four reaction steps to produce memantine hydrochloride with overall yields ranging from 54 to 77%. In this article, a simple, concise two-step synthesis of memantine hydrochloride from 1,3-dimethyl-adamantane via <i>N</i>-formamido-3,5-dimethyl- ...[more]

PMID: 32656430

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