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Synthesis of 1,2-Diamino-1,2-Diphenylbutane by Titanium Induced Reaction of Ammonia with Acetophenone

✍ Scribed by E. Volckaerts; H. J. Geise; F. Daelemans; J. Claereboudt

Publisher
Wiley (John Wiley & Sons)
Year
2010
Weight
315 KB
Volume
101
Category
Article
ISSN
0037-9646

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✦ Synopsis

Abstract

Reaction at room temperature of gaseous ammonia with acetophenone under the influence of low‐valent titanium ‐ prepared from TiCl~3~: LiAlH~4~ in the molar ratio 2 : 1 ‐ leads to formation of 2,3‐diamino‐2,3‐diphenylbutane in a synthetically useful yield (58 %). It is essential to simultaneously add NH~3~ and ketone keeping their ratio 1 : 1 until the ratio Ti: NH~3~: ketone = 1 : 1 : 1 is reached. Mass spectral characteristics and other spectroscopic properties of the new compound and of some side compounds are discussed. A plausible mechanism of the aminative reductive ketone coupling is given.

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