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

Participants

Reaction Conditions

Reaction Steps

4-(2-Chloroethyl)benzoic acid (1.00 g, 5.4 mmol) is dissolved in thionyl chloride (6.0 mL) and stirred at 50° C. for 30 min. The excess thionyl chloride is removed in vacuo and the residue is dissolved in dichloromethane (2 mL) to make a solution of the acid chloride. Triethylamine (656 mg, 6.5 mmol) and (S)(+)-1-(2-pyrrolidinylmethyl)pyrrolidine (1.00 g, 6.5 mmol) are dissolved in dichloromethane (30 mL) and cooled to 0° C. The acid chloride solution is added to this mixture at 0° C. and stirred at room temperature for 2 h. The reaction mixture is diluted with CH2Cl2, washed with brine, dried over Na2SO4, and evaporated. The crude product is purified by silica-gel column chromatography (CH2Cl2:2M NH3 in MeOH=40:1) to give 1.35 g (80%) of the title compound. MS (APCI+) 321 (M+H)+.

Provenance & Evidence