Journal of Organic Chemistry p. 677 - 681 (1989)
Update date:2022-07-30
Topics:
Fraenkel, Gideon
Gallucci, Judith
Rosenzweig, Howard S.
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.
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