p-Bromobenzenesulfonyl chloride → 4-Bromo-N-{5-(cis-3,5-dimethyl-1-piperazinyl)-2-[(phenylmethyl)oxy]phenyl}benzenesulfonamide

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Reaction Steps

A solution of 5-(cis-3,5-dimethyl-1-piperazinyl)-2-[(phenylmethyl)oxy]aniline (D39) (500 mg, 1.61 mmol) in dichloromethane (8 ml) and pyridine (8 ml) was added 4-bromobenzenesulfonyl chloride (820 mg, 3.21 mmol) and the resulting mixture stirred at room temperature, under an atmosphere of argon for 2 hours. The mixture was then reduced in vacuo, azeotroped with methanol and the residue partitioned between dichloromethane (75 ml) and saturated aqueous sodium hydrogen carbonate (75 ml). The layers were separated, the aqueous re-extracted with dichloromethane (50 ml) and the combined organic layers washed with brine (125 ml), dried over anhydrous magnesium sulphate, filtered and reduced in vacuo. The residue was purified by chromatography on silica gel (gradient: dichloromethane:methanol 25:1 to 10:1) to afford the title compound (D40). MS (ES+) m/e 530/532 [M+H]+.

Provenance & Evidence