Water → N-methoxy-N-methylcyclohexanecarboxamide

Participants

Reaction Steps

In a dried, flushed with nitrogen round bottom flask, N,O-dimethyl hydroxylamine hydrochloride (0.1 mol, 13.3 ml) was suspended in 200 ml anhydrous dichloromethane. To the resulting mixture triethylamine (0.22 mol, 30 ml) was added dropwise in ˜5 min while cooling by water (stirring became difficult because of salts formation). To the resulting mixture, while stirring under nitrogen and cooling by ice water, cyclohexanecarbonyl chloride was added dropwise in ˜15 min. The mixture was stirred overnight, washed with water (50 ml), saturated aqueous NH4Cl (50 ml), then brine (50 ml), dried over Na2SO4, and concentrated to give 17.8 g of crude product. Purification on 150 g silica gel, eluent hexanes-ethyl acetate, from 100:0 to 50:50, afforded 13.6 g (80%) of N-methyl-N-methoxy-cyclohexanecarboxamide as clear oil, Rf 0.44 (hexanes-EtOAc 1:1), 1H NMR (400 MHz, CDCl3) δ 3.67 (s, 3H, OCH3), 3.15 (s, 3H, NCH3), 2.65 (m, 1H, CH—CO), 1.8-1.6 (m, 5H, cyclohexyl), 1.5-1.4 (qm, 2H, cyclohexyl), 1.3-1.2 (m, 3H, cyclohexyl).

Provenance & Evidence