Synthesis 2005(4): 627-633  
DOI: 10.1055/s-2005-861798
PAPER
© Georg Thieme Verlag Stuttgart · New York

A General One-Pot, Three-Component Mono N-Alkylation of Amines and Amine Derivatives in Lithium Perchlorate/Diethyl Ether Solution

Akbar Heydari*, Hossein Tavakol, Saied Aslanzadeh, Jamshid Azarnia, Nafiseh Ahmadi
Chemistry Department, Tarbiat Modarres University, P. O. Box 14155-4838, Tehran, Iran
Fax: +98(21)8006544; e-Mail: akbar.heydari@gmx.de;
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Publikationsverlauf

Received 24 September 2004
Publikationsdatum:
03. Februar 2005 (eFirst)

Abstract

An efficient, general procedure for reductive monoalkyl­ation of amines and amine derivatives with aldehydes is reported. Treatment of aldehydes with primary amines, secondary amines, O-trimethylsilylhydroxylamine, and N,N-dimethylhydrazine in lithium perchlorate/diethyl ether and trimethylsilyl chloride, followed by BH3·NEt3 reduction, and straightforward workup afforded secondary amines, tertiary amines, N-substituted hydroxylamines, and hydrazines, respectively. Reductive alkylation of α-amino esters with aldehydes afforded the corresponding N-monoalkylated α-amino esters selectively.

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