Sesamol → N-Methylparoxetine

Participants

Reaction Steps

Sesamol (4.32 g, 31.2 mmol) was added to a solution of tetrabutylammonium hydroxide in isopropanol/methanol (0.1N, 342 mL), and the solvents were evaporated under vacuum to dryness. The residual tetrabutylammonium salt of sesamol was dissolved in acetonitrile (40 mL) and 4-(4-fluorophenyl)-3-chloromethyl-N-methyl-piperidine (CIPMA) (7.5 g, 31.2 mmol) was added. The reaction mixture was stirred with heating at reflux for 4 hours. After cooling, the reaction mixture was evaporated to dryness in vacuum and the residue was dissolved in toluene. The toluene solution was washed with 5% aq. sodium hydroxide and then with water. After drying with sodium sulfate and evaporation of the solvent in vacuum, N-methylparoxetine (8.1 grams) was obtained with yield 76%.

Provenance & Evidence