1,2-Dichloroethane → HCID 178502722, compound

Participants

Reaction Steps

EDC (2.87 g, 15.0 mmol) was added portionwise to a stirred solution of cis-4-(4-chlorobenzoyl)-cyclohexanecarboxylic acid (2.0 g, 7.5 mmol), DMAP (5 mg), HOBt (5 mg) and N,O-dimethylhydroxylamine hydrochloride (1.46 g, 15 mmol) in dichloromethane (40 mL). Triethylamine (2.28 g, 3.14 mL, 22.5 mmol) was added dropwise, and the reaction mixture was stirred at room temperature overnight. The resulting solution was poured into water, and extracted with ethyl acetate (3×). The combined organic phase was washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to give cis-4-(4-chlorobenzoyl)-cyclohexanecarboxylic acid, methoxy-methyl amide as a colorless oil (1.6 g. 69%); 1H NMR (CDCl3, 300 MHz) δ 7.82 (d, J=8.5 Hz, 2H,), 7.41 (d, J=8.5 Hz, 2H), 3.69 (s, 3H), 3.35 (quin, J=5 Hz, 1H), 3.16 (s, 3H), 2.80 (sept, J=4 Hz, 1H), 2.15 (m, 2H), 1.89 (m, 2H), 1.72 (m, 4H).

Provenance & Evidence