Triethylamine → [4-(2-chloroethyl)phenyl]-[(2S)-2-(pyrrolidin-1-ylmethyl)pyrrolidin-1-yl]methanone

Participants

Reaction Conditions

Reaction Steps

Add thionylchloride (6 mL) to 4-(2-chloroethyl)benzoic acid (1.00 g, 5.4 mmol) and stir at 50° C. for 30 min. Remove the excess thionylchloride in vacuo and dissolve the reside to dichloromethane (2 mL). Add this acid chloride solution to the mixture of triethylamine (656 mg, 6.5 mmol) and (S)(+)-1-(2-pyrrolidinylmethyl)pyrrolidine (1.00 g, 6.5 mmol) in dichloromethane (30 mL) at 0° C. and stir it at room temperature for 2 h. Dilute the reaction mixture and wash with brine, dry over sodium sulfate and remove the solvent. Purify the crude product by a silica-gel column chromatography (dichloromethane:2M ammonia in methanol=40:1) to give the title compound. 1.35 g (80%). Observed Mass 321.

Provenance & Evidence