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

Green Chemistry Pub Date: 2018-06-18 DOI: 10.1039/C8GC00863A

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
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