Diethyl Ether → N-propionyl-3-(3-methoxyphenyl)pyrrolidone

Participants

Reaction Conditions

Reaction Steps

3-(3-methoxyphenyl)pyrrolidine (8.86 g, 0.050 mol) and triethylamine (5.57 g, 0.055 mol) was dissolved in 500 ml of dry ether. The solution was cooled to 0° C and propionyl chloride (5.09 g, 0.055 mol) was added dropwise with stirring. The reaction mixture was then allowed to acquire ambient temperature, whereafter it was refluxed for 30 minutes. Triethylamine hydrochloride was filtered off, and the filtrate was evaporated leaving 11.7 g (100%) of crude N-propionyl-3-(3-methoxyphenyl)pyrrolidone, which was used in the next reaction step without further purification. The crude amide (11.7 g, 0.050 mol) was reduced with LiAlH4 (2.85 g, 0.075 mol) in refluxing ether (200 ml) for 24 hours. Workup of the reaction mixture afforded 10 g of product, which upon distillation in vacuo yielded 9.1 g (83%) of N-propyl-3-(3-methoxyphenyl)-pyrrolidine b.p. 85-86° C/O.1 mm Hg. MS: m/e 219 (M +, 12%) 190 (M--C2H5, 100%).

Provenance & Evidence