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Issue 14, 2018
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Selective synthesis of mono- and di-methylated amines using methanol and sodium azide as C1 and N1 sources

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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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Publication details

The article was received on 17 Mar 2018, accepted on 17 Jun 2018 and first published on 18 Jun 2018


Article type: Paper
DOI: 10.1039/C8GC00863A
Citation: Green Chem., 2018,20, 3339-3345

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    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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