Issue 14, 2018

Selective synthesis of mono- and di-methylated amines using methanol and sodium azide as C1 and N1 sources

Abstract

A Ru(II) complex mediated synthesis of various N,N-dimethyl and N-monomethyl amines from organic azides using methanol as a methylating agent is reported. This methodology was successfully applied for a one-pot reaction of bromide derivatives and sodium azide in methanol. Notably, by controlling the reaction time several N-monomethylated and N,N-dimethylated amines were synthesized selectively. The practical applicability of this tandem process was revealed by preparative scale reactions with different organic azides and synthesis of an anti-vertigo drug betahistine. Several kinetic experiments and DFT studies were carried out to understand the mechanism of this transformation.

Graphical abstract: Selective synthesis of mono- and di-methylated amines using methanol and sodium azide as C1 and N1 sources

Supplementary files

Article information

Article type
Paper
Submitted
17 mar 2018
Accepted
17 jún 2018
First published
18 jún 2018

Green Chem., 2018,20, 3339-3345

Selective synthesis of mono- and di-methylated amines using methanol and sodium azide as C1 and N1 sources

K. Chakrabarti, A. Mishra, D. Panja, B. Paul and S. Kundu, Green Chem., 2018, 20, 3339 DOI: 10.1039/C8GC00863A

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