Dimethyl Sulfoxide → HCID 59367764, compound

Oxalyl chloride (3.3 mmol, 2 eq.) was dissolved in methylene chloride and DMSO (4 eq) was added under argon at −78° C. and the reaction mixture was then stirred at this temperature for 15 min. (1-(2-Chloro-6-methylphenylsulfonyl)-piperidin-2-yl)methanol (1.65 mmol) was dissolved in methylene chloride (15 ml) and the solution was added dropwise to the reaction solution at −78° C. The resulting mixture was stirred for 1 h. Triethylamine (8.25 mmol, 5 eq) was then added and the reaction solution was warmed to room temperature and stirred for 1 h. It was then diluted with methylene chloride (10 ml) and washed with saturated ammonium chloride solution (10 ml), water (2×20 ml) and saturated sodium chloride solution (10 ml). The organic phase was dried over sodium sulfate and the filtrate was concentrated to dryness under reduced pressure. The crude product was employed in the next stage without further purification. Yield: 80%

1. additionthe solution was added dropwise to the reaction solution at −78° C
2. stirringstirred for 1 h
3. washwashed with saturated ammonium chloride solution (10 ml), water (2×20 ml) and saturated sodium chloride solution (10 ml)
4. dry with materialThe organic phase was dried over sodium sulfate
5. concentrationthe filtrate was concentrated to dryness under reduced pressure
6. customThe crude product was employed in the next stage without further purification

ORD record

ord-33008ece2d4e44fbb8b96701db7ee264

Source dataset

uspto-grants-2012_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08119805B2