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Synthesis 2011(3): 490-496  
DOI: 10.1055/s-0030-1258384
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Catalyst-Free One-Pot Reductive Alkylation of Primary and Secondary Amines and N,N-Dimethylation of Amino Acids Using Sodium Borohydride in 2,2,2-Trifluoroethanol

Mahmood Tajbakhsh*a, Rahman Hosseinzadeha, Heshmatollah Alinezhada, Somayeh Ghaharia, Akbar Heydarib, Samad Khaksarc
a Department of Chemistry, University of Mazandaran, P. O. Box 453, Babolsar 47415, Iran
Fax: +98(112)5342350; e-Mail: Tajbaksh@umz.ac.ir;
b Chemistry Department, Tarbiat Modares University, P. O. Box 14115-175, Tehran 18716, Iran
c Chemistry Department, Islamic Azad University, Ayatollah Amoli Branch, P.O. Box 678, Amol, Iran
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Publication History

Received 9 November 2010
Publication Date:
28 December 2010 (online)

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Abstract

A simple and convenient procedure for the reductive alkylation of primary and secondary amines and N,N-dimethylation of amino acids is described using sodium borohydride as a reducing agent in 2,2,2- trifluoroethanol without use of a catalyst or any other additive. The solvent can be readily recovered from reaction products in excellent purity for direct reuse.

Key words

reductive amination - 2,2,2-trifluoroethanol - sodium borohydride - reductive methylation