HCID 18619288, compound → Hexahydro-1,4,6-trimethyl-1H-1,4-diazepin-6-amine

Participants

Reaction Steps

6-Nitro-1,4,6-trimethyldiazacycloheptane (13.1 g, 70 mmol) was was dissolved in absolute ethanol (20 ml) and 2 spatulas of Raney nickel added. The mixture was hydrogenated at approx. 1.1 atmospheres hydrogen pressure until no more hydrogen was taken up. It was filtered over a small pad of Celite and the filtrate evaporated and distilled to give the free amine as a colourless oil (7.95 g, 72%) b.p.>70° C./0.1 mm. IR (film) 3348 (s), 2945 (s), 2813 (s), 1670 (m), 1538 (m), 1462 (s), 1376 (m), 1284 (m), 1093 (s) cm−1. 1H NMR (CDCl3) δ 1.00 s(3H), 2.32 s(6H), 2.28 and 2.44 and 2.63, 3 m (10H including N—H). 13C NMR (CDCl3) δ 26.37, 48.91, 52.54, 60.35, 71.17. MS (FAB+) 158.1 [M+H]+.

Provenance & Evidence