Sodium hydride → 1-{3-[3-(3,4-Dimethoxyphenyl)propoxy]propyl}-pyrrolidine

Participants

Reaction Steps

A To a solution of 1-(3-hydroxypropyl)pyrrolidine (631 mg) in toluene (10 mL) stirred at a temperature close to 0° C. is added sodium hydride (208 mg, 60% wt in paraffin). The mixture is stirred for three hours at room temperature, cooled to a temperature close to 0° C. and 3-(3,4-dimethoxyphenyl)propan-1-ol mesylate (750 mg), 15-crown-5 (30 μL), tetrabutylammonium iodide (8 mg) are added. The mixture is heated at reflux for 30 min, stirred overnight at room temperature and diluted with diethyl oxide. The organic layer is washed twice with water, dried over magnesium sulphate, concentrated under reduced pressure and purified by chromatography over silica gel with dichloromethane/methanol 94/6 as eluent. Fractions containing the expected product are pooled, concentrated under reduced pressure, dissolved in diethyl oxide and salted with a solution of 68.8 mg of oxalic acid in 1 mL of acetone. The precipitate is filtered, rinsed with diethyl oxide and dried to give 110 mg of 1-{3-[3-(3,4-dimethoxyphenyl)propoxy]propyl}-pyrrolidine, oxalate as a solid melting at 78-79° C.

Provenance & Evidence