Triethylamine → 4-[(glycylamino)methyl]-1-[4-(N-phenylcarbamoyl)benzyl]piperidine

Participants

Reaction Conditions

Reaction Steps

To a mixture of 4-[{N-(9-fluorenylmethyloxycarbonyl)glycyl}aminomethyl]piperidine (1.27 g, 2.96 mmol), Et3N (1.25 mL, 8.88 mmol), KI (50 mg, 0.30 mmol) and CH3CN (200 mL) was added dropwise a solution of 4-(N-phenylcarbamoyl)benzyl chloride (800 mg, 3.26 mmol) in CH3CN (100 mL). The mixture was stirred at room temperature for 19 h and at 60° C. for 5 h. Concentration and column chromatography (SiO2, 5% CH3OH/CH2Cl2-Et3N:CH3OH:CH2C2=2:2:96) afforded 4-{(glycylamino)methyl}-1-{4-(N-phenylcarbamoyl)benzyl}piperidine (340 mg, 30%).

Provenance & Evidence