4-Methylmorpholine → HCID 42635255, compound

Participants

Reaction Conditions

Reaction Steps

(1-Methylpiperidin-4-yl)methanol (1.00 g, 7.74 mmol) was dissolved in DCM (20 mL) and cooled to 0° C. NMM (0.94 mL, 8.51 mmol) and 4-nitrophenyl chloroformate (1.56 g, 7.74 mmol) were added. The reaction mixture was stirred at 0° C. for 20 minutes and then added to a solution of 4-(4-methoxyphenyl)piperazine (1.64 g, 8.51 mmol) and DIPEA (2.02 mL, 11.01 mmol) in DMF (30 mL). The reaction mixture was stirred at room temperature for 4 h and then concentrated in vacuo. The residue was dissolved in EtOAc (200 mL) and washed sequentially with 1 M aq NaOH solution (5×100 mL), brine (100 mL), dried (MgSO4) and concentrated in vacuo. The residue was purified by reverse phase chromatography (gradient eluting with MeOH in water, with 1% formic acid in each solvent, 0-30%). The resulting residue was dissolved in DCM (70 mL) and stirred with solid K2CO3 for 20 minutes, filtered and concentrated in vacuo to give (1-methylpiperidin-4-yl)methyl 4-(4-methoxyphenyl)piperazine-1-carboxylate (0.277 g, 10.3%) as an off-white solid.

Provenance & Evidence