Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Reaction of N-Haloamide. XVI. Reaction of N, N-Dichlorophenylacetamide with Aliphatic Secondary Amines
HIROMI TERAUCHISHOJI TAKEMURAYOSHIO UENO
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1972 Volume 20 Issue 11 Pages 2477-2480

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Abstract
Secondary amines such as diethylamine (II), piperidine (IV), and 2-ethylpiperidine (VI) were allowed to react with N, N-dichlorophenylacetamide (I) to give N, N-diethyl-N'-benzylurea (III), benzylcarbamoylpiperidine (V), and benzylcarbamoyl-2-ethylpiperidine (VII), respectively. Three moles of amines were consumed to complete the reactions, that is, urea derivatives, amine hydrochlorides, and N-chloroamines were produced, simultaneously. The latters were reduced with sodium bisulfite to give amine hydrochlorides. The mechanism of these reaction was also discussed.
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© The Pharmaceutical Society of Japan
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