Triethylamine → 2-(4-Methylpiperazin-1-yl)-ethyl 4-(2-methylphenyl)piperazine-1-carboxylate

Participants

Reaction Steps

2-(4-Methylpiperazin-1-yl)ethyl 4-nitrophenyl carbonate (Intermediate 4; 866 mg, 2.8 mmol) was dissolved in DMF (20 mL). NEt3 (1.5 mL, 10.8 mmol) and 4-(2-methyl-phenyl)piperazine dihydrochloride (704 mg, 2.8 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 resulting residue was dissolved in EtOAc (50 mL) and washed with 1 M aq Na2CO3 solution (5×50 mL), dried (MgSO4) and concentrated in vacuo. The residue was purified by normal phase column chromatography (eluting with DCM, followed by a 200:8:1 mixture of DCM:EtOH:NH3) to give 2-(4-methylpiperazin-1-yl)-ethyl 4-(2-methylphenyl)piperazine-1-carboxylate (308 mg, 32%) as a yellow oil.

Provenance & Evidence