p-Bromobenzenesulfonyl chloride → HCID 178483911, compound

Participants

Reaction Steps

To 158 mg (0.5 mmol) of trans-N-(3-hydroxy-propyl)-N-methyl-3-(4-methylamino-cyclohexyloxy)-propionamide-hydrochloride in 3 mL of CH2Cl2 were added 0.44 mL (2.6 mmol, 5 eq) of N,N-diisopropylethylamine followed by 0.14 mg (0.56 mmol, 1.1 eq) of 4-bromo-benzenesulfonyl chloride. The mixture was stirred at RT for 1 h and the organic phase was extracted with 1M KHSO4. The combined organic phases were washed with brine, dried over Na2SO4 and evaporated. Column chromatography on silica gel with a gradient of CH2Cl2:MeOH 98:2 to 95:5 yielded 101 mg (40%) of trans-3-{4-[(4-bromo-benzenesulfonyl)-methyl-amino]-cyclohexyloxy}-N-(3-hydroxy-propyl)-N-methyl-propionamide as colorless oil, MS: 491 (MH+,1Br).

Provenance & Evidence