Efficient Preparation of Cis Vicinal Tertiary Diamines from 2-Hydroxy Ketones in Two Steps

Article abstract of DOI:10.1021/jo00264a031

Cyclic (C5 and C6) cis vicinal tertiary diamines are efficiently prepared by catalytic hydrogenation, Pd(C), of the corresponding N-substituted amino enamines, e.g. 6.The latter are obtained by p-toluenesulfonic acid catalyzed condensation of secondary amines with cyclic 2-hydroxy ketones in refluxing benzene under Dean-Stark conditions or from the N-substituted 2-amino ketones.For example cis-1,2-dipyrrolidinocyclohexane has been obtained from adipoin in 69percent overall yield, isolated.