2-(4-Chlorobenzyl)pyrrolidine → HCID 131712299, compound

Participants

Reaction Steps

Add a solution of 37.6 g of dibenzoyl-L-tartaric acid in 250 ml of acetone to 19.57 g of 2-(4-chlorobenzyl)pyrrolidine dissolved in 200 ml of acetone. Allow the resulting reaction mixture to stand for 12 hours and then filter off the precipitated crystals (25.8 g); [α]58920 =-84.7° (25 mg/ml in methanol). Recrystallize from 75 ml methanol/100 ml acetone to obtain 15.43 g of (-)-2-(4-chlorobenzyl)pyrrolidine dibenzoyl tartrate (m.p. 178° to 179°); [α]58920 =-88° (25 mg/ml in methanol). Stir 14.85 g of this salt with sodium hydroxide solution/diethyl ether until two clear phases form. Collect the ether phase and dry it over sodium sulfate. Thereafter, concentrate the dried ether phase to obtain the title compound as a colorless oil (5.0 g). Treat the colorless oil with methanol/ethereal hydrochloric acid to convert it into 4.83 g of the corresponding hydrochloride (m.p. 216° to 218°); [α]58920 =-31.4° (25 mg/ml in methanol).

Provenance & Evidence