Cl.[CH3:2][S:3]([CH:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1)(=[O:5])=[O:4].Br[CH2:13][CH2:14][OH:15].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:2][S:3]([CH:6]1[CH2:11][CH2:10][N:9]([CH2:13][CH2:14][OH:15])[CH2:8][CH2:7]1)(=[O:5])=[O:4]A mixture of 4-(methylsulfonyl)piperidine hydrochloride (900 mg, 4.51 mmol), 2-bromoethanol (1126 mg, 9.01 mmol) and potassium carbonate (1869 mg, 13.52 mmol) in acetonitrile (4 mL) was heated up at 60° C. for 13 hours. The reaction mixture was cooled to room temperature and concentrated under reduced pressure to provide the crude, the crude was purified by 0-35% ethyl acetate/methanol to provide the desired product as colorless oil (620 mg, 66%). LCMS: m/e 208.1 (M+H)+, 0.27 min (method 6).
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