4-(Dimethylamino)Benzaldehyde → 1-(4-(dimethylamino)benzyl)-4-[{N-(3-(trifluoromethyl)benzoyl)glycyl}aminomethyl]piperidine

Participants

Reaction Conditions

Reaction Steps

A methanol (1.0 mL) solution of 4-[[N-(3-(trifluoromethyl)benzoyl)glycyl]aminomethyl]piperidine (20.0 mg, 0.058 mmol) and NaBH3CN (16.5 mg) were added to a 5% acetic acid solution (1.0 mL) of 4-(dimethylamino)benzaldehyde (30.4 mg, 0.204 mmol), and the resulting mixture was stirred at 60° C. for 19 hours. The solvent was evaporated to provide a solid. Acetonitrile (2.0 mL) and phenyl isocyanate (6.9 mg, 0.048 mmol) were added to the solid, and resulting mixture was stirred at 25° C. for 1 hour. The reaction mixture was loaded onto a Varian™ SCX column and washed with methanol (20 mL). The obtained crude product was eluted with a 2 M NH3-methanol (6 mL), and the eluate was concentrated to thereby afford 1-[4-(dimethylamino)benzyl]-4-[[N-(3-(trifluoromethyl)benzoyl)glycyl]aminomethyl]piperidine (Compd. No. 937) as an off-white oil (13.5 mg, 49%). The purity was determined by RPLC/MS (87%). ESI/MS m/e 477.3 (M++H, C25H31F3N4O2).

Provenance & Evidence