Triethylamine → HCID 58561856, compound

Participants

Reaction Steps

To a stirred ice-cold solution of tert-butyl piperazine-1-carboxylate (C1, 10.0 g, 53.76 mmol) in CH2Cl2 (50 mL) at 0° C. was added Et3N (22.66 mL, 161.29 mmol) and a solution of 1-methyl-1H-imidazole-4-sulfonyl chloride (11.61 g, 64.51 mmol) in CH2Cl2 (50 mL) drop wise over 30 minutes while maintaining the temperature of the reaction mixture below 5° C. and under an atmosphere of N2. The reaction mixture was warmed to room temperature and stirred for an additional 5 h then quenched with a saturated solution of NaHCO3 (50 mL). The aqueous mixture was extracted with CH2Cl2 (3×100 mL), and the combined organic extracts were washed with brine (1×50 mL), dried (Na2SO4), filtered and concentrated under reduced pressure to give a crude solid. The solids were suspended in Et2O and stirred for 30 minutes at room temperature then filtered, washed with cold diethyl ether and dried under vacuum to afford tert-butyl 4-(1-methyl-1H-imidazol-4-ylsulfonyl)piperazine-1-carboxylate (36) as an off-white solid (16.8, 95%): 1H NMR (300 MHz, CDCl3) δ (dd, J=1.5 Hz, 14.56 Hz, 2H), 3.76 (s, 3H), 3.55-3.45 (m, 4H), 3.20-3.10 (m, 4H), 1.43 (s, 9H); MS (ESI+) m/z 331 (M+H).

Provenance & Evidence