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1 2004

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A Facile Synthesis of Primary and Secondary Amines

Łankiewicz L., Rój A., Szymańska A., Wiczk W.

Polish Journal of Chemistry

2004

Vol. 78 / nr 8

1067-1072

A facile synthesis of primary amines (R-CH2-NH2, where R = napht-2-yl, anthr-9-yl, phenyl, p-nitrophenyl) and secondary amines (R-NH-R', where R is as mentioned above for primary amines and R'= methyl) is described. The primary amines were obtained by alkylation of di-tert-butyl imidodicarbonate (Boc2NH) under phase-transfer catalysis (PTC) conditions, followed by acidolytic removal of the amine protecting groups. The secondary amines were obtained from the appropriate primary amines by alkylation of their N-tert-butoxycarbonyl derivatives (Boc-NH-R), followed by Boc group acidolysis. It is worth emphasizing that the substrates for synthesis of secondary amines (Boc-NH-R) were obtained via selective removal of one of the tert-butoxycarbonyl groups from the alkylated di-tert-butyl imidodicarbonates (Boc2N-R).