Synthesis of N-Aminated Salts of Aliphatic tert-Amines, (Trialkyl)amidines, and (Pentaalkyl)guanidines by Electrophilic Amination in an Ethereal Solvent.

Hikaru Fujita, Takanari Arai, Munetaka Kunishima

Chemical & pharmaceutical bulletin 2022

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The electrophilic amination of nitrogen-based nucleophiles, including strong organic bases, was conducted in an Et2O solvent using O-(mesitylenesulfonyl)hydroxylamine. Aliphatic tert-amines and N,N,N'-(trialkyl)amidines rapidly formed precipitates of the corresponding aminated salts in high yields. The amination of the highly basic and sterically hindered N,N,N',N',N″-(pentaalkyl)guanidines was achieved under modified conditions, although the yields were moderate because of a competing side reaction caused by the acid-base equilibrium.

Citation

Hikaru Fujita, Takanari Arai, Munetaka Kunishima. Synthesis of N-Aminated Salts of Aliphatic tert-Amines, (Trialkyl)amidines, and (Pentaalkyl)guanidines by Electrophilic Amination in an Ethereal Solvent. Chemical & pharmaceutical bulletin. 2022;70(1):85-88