Tetrahydrofuran → HCID 67647433, compound

Participants

Reaction Steps

Combine 2-[1-(3,4,5-trimethoxy-benzoyl)-3-(3,4-dimethyl-phenyl)-pyrrolidin-3-yl]-ethyl-methanesulfonate (3.0 g, 6.1 mmol) and tetrahydrofuran (45 mL)/water (15 mL). Add 4-phenyl-piperidine-4-carboxylic acid amide hydrochloride (2.2 g, 9.14 mmol) and potassium carbonate (2.6 g, 18.8 mmol). Heat to reflux. After 80 hours, evaporate the reaction mixture in vacuo to remove most of the tetrahydrofuran and then extract with dichloromethane. Separate the organic layer and extract with water. Dry the organic layer over MgSO4, filter, and concentrate in vacuo to give a residue. Chromatograph the residue on silica gel eluting sequentially with ethyl acetate, 3% methanol/dichloromethane, 6% methanol/dichloromethane, and then 10% methanol/dichloromethane to give the title compound: Rf =0.44 (silica gel, 10% methanol/dichloromethane).

Provenance & Evidence