Hydrochloric Acid → 2-Chlorobenzenesulfonic acid 3-[(piperidin-3-yl)methoxy]-5-methylphenyl ester

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Reaction Steps

2-Chlorobenzenesulfonic acid 3-[[N-(tert-butoxycarbonyl)piperidin-3-yl]methoxy]-5-methylphenyl ester (745 mg, 1.5 mmol), as prepared in the preceding step, was treated with 20 mL of 4N HCl in 1,4-dioxane at room temperature for 2 h. The solvent was removed in vacuo and the residue was purified by flash column chromatography (10% methanol in methylene chloride saturated with NH3) to give the title compound as a colorless syrup (565 mg, 94%). 1H-NMR (300 MHz, CDCl3) δ 1.45 (t, 1H), 1.94 (m, 3H), 2.23 (s, 3H), 2.45 (bs, 1H), 2.77 (t, 2H), 3.50 (dd, 2H), 3.76 (m, 2H), 6.46 (d, 1H), 6.55 (d, 2H), 7.40 (dd, 1H), 7.62 (m, 2H), 7.96 (dd, 1H). Mass spectrum (MALDI-TOF, sinapinic acid matrix) calcd. for C19 H22NO4SCl: 396.1 (M+H), 418.1 (M+Na), Found: 395.8, 418.2.

Provenance & Evidence