Dimethyl Sulfoxide → HCID 13925233, compound

Participants

Reaction Conditions

Reaction Steps

To a cooled (−78° C.) solution of oxalyl chloride (0.839 g, 6.73 mmol) in dry DCM (5 mL) was added dimethylsulfoxide (1.05 g, 13.46 mmol) dropwise. The mixture was stirred for 10 min at −78° C., 1-benzyl-4-(2-methoxyphenyl)piperidin-3-ol (1.0 g, 3.367 mmol) in DCM (10 mL) was added and stirring continued for a further 20 min at −78° C. Triethylamine (3.3 ml, 23.56 mmol) was added, the reaction mixture was stirred for 15 min at −78° C., warmed to room temperature and diluted with water. The organic layer washed with 2N HCl (50 mL), 10% aqueous sodium bicarbonate solution, brine and dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to afford 1-benzyl-4-(2-methoxyphenyl)piperidin-3-one (0.7 g, 70%) which was used in the next step without further purification. 1H NMR (200 MHz, CDCl3): δ 2.72 (m, 2H) 2.91-3.045 (m, 2H), 3.71 (m, 2H), 3.80 (s, 2H), 6.87-6.99 (m, 2H), 7.12 (dd, J=7.5, 1.7 Hz, 1H), 7.18-7.45 (m, 6H); m/e=295 (M+1).

Provenance & Evidence