Cyclohexanone → HCID 59347798, compound

Participants

Reaction Steps

The title compound was prepared in two stages from (i) dimethylamine hydrochloride (3.26 g, 0.04 mol), cyclohexanone (3.9 g, 0.04 mol) and potassium cyanide (2.60 g, 0.04 mol) in water (25 ml) in a similar manner to that described in D1 to make 1-(dimethylamino)cyclohexanecarbonitrile (6.6 g, 100%). This was reacted directly in (ii) with phenyl lithium in dibutyl ether (10.5 ml of a 1.9M solution, 0.02 mol) in THF (30 ml) followed by sodium borohydride (1.51 g, 0.04 mol) in a similar manner to that described in D2 to afford the title compound (2.5 g, 36%). 1H NMR (CDCl3) δ: 0.85 (1H, m), 1.00 (1H, m), 1.25 (2H, m), 1.35-1.60 (6H, br m), 1.70 (1H, m), 2.10 (1H, m), 2.46 (6H, s), 4.15 (1H, s), 7.20-7.32 (5H, m).

Provenance & Evidence