4-Toluenesulfonyl chloride → HCID 69422321, compound

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A mixture of cis-1-methylamino-3-(4-methylpiperidin-1-yl)cyclopentane dihydrochloride (24.5 mg, 0.091 mmol) and 4-toluenesulfonyl chloride (27.9 mg, 0.146 mmol) in dichloromethane (2 ml) and 1M aqueous sodium hydroxide (2 ml) was rapidly stirred at room temperature overnight (22 hours). The phases were separated and the aqueous extracted with more dichloromethane (5 ml). The combined organics were dried (MgSO4) and evaporated. The residue was dissolved in methanol-ethyl acetate and treated with excess 1M hydrogen chloride in diethyl ether. Recrystallization of the resulting solid from methanol-ethyl acetate gave the title compound (31.5 mg, 89%) as a white solid; δH (400 MHz, CD3OD) 1.00 (3H, d, J 6.1 Hz), 1.43 (2H, m), 1.62-1.83 (5H, m), 1.91 (2H, m), 2.04-2.18 (2H, m), 2.43 (3H, s), 2.77 (3H, s), 2.89 (2H, m), 3.50 (3H, m), 4.41 (1H, m), 7.40 (2H, d, J 8.5 Hz), 7.71 (2H, d, J 8.5 Hz); m/z (ES+) 351 ([M+H]+, 100%).

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