2-Chlorobenzenesulfonic acid 3-[2-[N-(tert-butoxycarbonyl)piperazin-4-yl]ethoxy]phenyl ester → 2-Chlorobenzenesulfonic acid 3-[(piperazin-4-yl)ethoxy]phenyl ester

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Reaction Steps

2-Chlorobenzenesulfonic acid 3-[2-[N-(tert-butoxycarbonyl)piperazin-4-yl]ethoxy]phenyl ester (994 mg, 2.0 mmol), as prepared in the preceding step, was treated with 4N HCl (40 mL in 1,4-dioxane) and stirred at room temperature for 2 h. After concentrating in vacuo, the residue was purified by flash column chromatography (10% methanol in methylene chloride saturated with NH3) to give the title compound as a white foam (705 mg, 88%). 1H-NMR (300 MHz, CDCl3) δ 2.00 (bs, 1H), 2.54 (t, 4H), 2.76 (t, 2H), 2.93 (t, 4H), 4.02 (t, 2H), 6.72 (m, 2H), 6.78 (dd, 1H), 7.16 (t, 1H), 7.37 (dt, 1H), 7.61 (m, 2H), 7.95 (dd, 1H). Mass spectrum MALDI-TOF, sinapinic acid matrix) calcd. for C18H21N2O4SCl: 397.1 (M+H). Found: 397.6.

Provenance & Evidence