Diisopropylethylamine → HCID 66650868, compound

Participants

Reaction Steps

2-(4-Methylpiperazin-1-yl)ethyl 4-nitrophenyl carbonate (Intermediate 4; 680 mg, 2.2 mmol) was dissolved in DMF (20 mL). DIPEA (0.76 mL, 4.4 mmol) and 4-(3,4-dichlorophenyl)piperazine (508 mg, 2.2 mmol) were added and the reaction mixture was stirred at room temperature for 24 hours, and the reaction mixture was then concentrated in vacuo. The residue was purified by normal phase column chromatography (eluting with DCM, followed by a 400:8:1 mixture of DCM:EtOH:NH3, followed by a 200:8:1 mixture of DCM:EtOH:NH3) followed by reverse phase column chromatography (gradient eluting with MeOH in water, with 1% formic acid in each solvent, 0-100%). The residue was dissolved in DCM (10 mL) and 2M HCl in Et2O (3 mL) was added. The reaction mixture was then concentrated in vacuo to give 2-(4-methylpiperazin-1-yl)ethyl 4-(3,4-dichlorophenyl)piperazine-1-carboxylate trihydrochloride (182 mg, 17%) as a white solid.

Provenance & Evidence