Potential neuroleptics of the orthopramide series; Synthesis of N-substituted 5-(aminosulfonyl)-2-methoxybenzamides

1 January 1987

journal article
Published by Institute of Organic Chemistry & Biochemistry in Collection of Czechoslovak Chemical Communications

Vol. 52 (8) , 2095-2106
https://doi.org/10.1135/cccc19872095

Abstract

The mixed anhydride of 5-(aminosulfonyl)-2-methoxybenzoic acid (VII) and monoethyl carbonate reacted with benzylamine, 1-methylpiperazine, and 1-benzylpiperazine to give the 5-(aminosulfonyl)-2-methoxybenzamides II, IV, and V. Heating the ethyl ester X with 4-amino-1-methyl-piperidine resulted in the amide III. Reaction of 5-(chlorosulfonyl)-2-methoxybenzoyl chloride (XI) with 1-benzylpiperazine afforded 5-(4-benzylpiperazinosulfonyl)-2-methoxybenzoic acid 4-benzylpiperazide (VI). Compounds II-VI are analogues of the antidopaminergic and antiemetic agent sulpiride (I) but only benzylpiperazides V and VI showed indications of psychotropic activity of the neuroleptic type.

Keywords

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