Dimethyl Sulfoxide → HCID 59438442, compound

Participants

Reaction Steps

To a −50° C. solution of 11 ul (0.21 mmol) oxalyl chloride in 0.8 ml dichloromethane was added a solution of 17.2 ul DMSO in 0.2 ml dichloromethane over a period of 15 minutes. The reaction mixture was stirred for 10 minutes, after which a solution of 50 mg (0.11 mmol) rac-N-(5-hydroxy-1-methyl-3-phenyl-piperidin-3-yl)-2-methoxy-6-methylsulfanyl-4-trifluoromethyl-benzamide (example 51) in 0.8 ml dichloromethane was added over a period of 15 minutes. After 30 min stirring, 77 ul (0.55 mmol) triethylamine was added. The reaction mixture was stirred for 15 minutes, then allowed to warm to room temperature and quenched with water and the aqueous layer was extracted with dichloromethane. The combined extracts were dried over sodium sulfate, filtered and concentrated in vacuo. The crude product was purified on silica gel (Eluent: Heptane/ethyl acetate 0 to 15%) to provide 44 mg (89%) of the title compound as a white foam. MS (m/e): 453.1 (MH+).

Provenance & Evidence