Acetic Acid → Benzenemethanamine, N-cyclohexyl-

Participants

Reaction Steps

To a stirred solution of cyclohexylamine (9.34 g) in methanol (300 ml) was added benzaldehyde (10.0 g) followed by activated 3 Å molecular sieves. After 1 h, sodium cyanoborohydride (7.13 g) was added followed by the dropwise addition of acetic acid (9.2 ml), and the reaction was stirred overnight. The reaction mixture was filtered through hiflo, the solvent removed in vacuo and the resulting white solid was heated under reflux in 5M potassium hydroxide solution for 30 mins. The product was extracted into dichloromethane (3×100 ml) and the combined organic layers were washed with brine (100 ml), dried over sodium sulphate and the solvent was removed in vacuo to give a clear oil. The product was purified by column chromatography (eluting with ethyl acetate) then distillation; bpt=137° C. at 1.0 mbarr. 1H NMR (360 MHz, D6 -DMSO) δ0.94-1.24 (5H, m), 1.48-1.88 (5H, m), 2.32 (1H, m), 2.32 (1H, m), 3.10 (2H, s(b)), 3.72 (2H, s), 7.14-7.40 (5H, m).

Provenance & Evidence