Triethylamine → 2-Chlorobenzenesulfonic acid 3-[[1-(aminoiminomethyl)piperidin-4-yl]methoxy]phenyl ester

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Reaction Steps

A solution of 2-chlorobenzenesulfonic acid 3-[(piperidin-4-yl)methoxy]phenyl ester (191 mg, 0.5 mmol), as prepared in the preceding step, in DMF (10 mL) containing triethylamine (0.2 mL) and aminoiminomethanesulfonic acid (124 mg, 1.0 mmol) was stirred at room temperature overnight. The DMF was concentrated in vacuo and the residue was purified by flash column chromatography (90: 10 methylene chloride:methanol saturated with NH3) to give the title compound as a white foam (105 mg, 49%). 1H-NMR (300 MHz, CDCl3 /DMSO)-d6) δ 1.38 (m, 2H), 1.88 (d, 2H), 2.08 (m, 1H), 3.00 (t, 2H), 3.79 (d, 2H), 4.05 (dd, 2H), 6.61 (dd, 1H) 6.77 (t, 1H), 6.79 (dd, 1H), 7.20 (t, 1H), 7.37 (bs, 3H), 7.50 (m, 1H), 7.92 (d, 2H). Mass spectrum (MALDI-TOF, sinapinic acid matrix) calcd. for C19H22 N3O4SCl: 424.1(M+H), 446.1 (M+Na), Found: 424.3, 446.6

Provenance & Evidence