1-Methylpiperazine → Hydrochloric Acid

Participants

Reaction Steps

Following general procedure 36B: Used 1-(cyclopropylmethyl)-2-(4-ethoxybenzyl)-1H-benzimidazole-5-sulfonyl chloride (from 0.2 mmol of aniline precursor), 1-methylpiperazine (0.4 mmol) pyridine (0.5 mL) in CH2Cl2 (4 mL). The resulting mixture was stirred at room temperature overnight. Isolated the desired product as the HCl salt after column chromatography and treatment with 1 M HCl solution in diethyl ether (59 mg, 75%). 1H NMR (400 MHz, CD3OD): δ 8.02 (s, 1H), 7.71 (d, J=8.6 Hz, 1H), 7.64 (d, J=8.6 Hz, 1H), 7.13 (d, J=8.8 Hz, 2H), 6.83 (d, J=8.8 Hz, 2H), 4.80 (s, 3H), 4.31 (s, 2H), 4.10 (d, J=7.2 Hz, 2H), 3.95 (q, J=8.0 Hz, 2H), 3.04–2.96 (m, 4H), 2.50–2.44 (m, 4H), 1.32 (t, J=8.0 Hz, 3H), 1.08–0.98 (m, 1H), 0.47–0.43 (m, 2H), 0.31–0.26 (m, 2H). MS (ESI) (M+1)+: 469. Anal. Calcd for C25H32N4O3S.2.7HCl.0.4H2O: C, 52.29; H, 6.23; N, 9.76. Found: C, 52.54; H, 6.21; N. 8.67.

Provenance & Evidence