N-(2-((1-(4-chlorobenzyl)piperidin-4-yl)methylamino)-2-oxoethyl)-2-amino-5-(trifluoromethyl)benzamide → 4-[[N-(2-amino-5-trifluoromethylbenzoyl)glycyl]aminomethyl]piperidine

Participants

Reaction Conditions

Reaction Steps

A suspension of 1-(4-chlorobenzyl)-4-[{(N-(2-amino-5-trifluoromethylbenzoyl)glycyl)amino}methyl]piperidine (447 mg, 0.93 mmol) and Pd(OH)2 (60 mg, 0.23 mmol) in 5% HCO2H/methanol (10 mL) was stirred at 50° C. for 14 h. The Pd catalyst was filtered off through Celite, and the filtrate was concentrated. To the residue was added 1 N aqueous NaOH solution (15 mL) and the mixture was extracted with ethyl acetate (30 mL×3). The combined extracts were dried over anhydrous sodium sulfate, filtered, and concentrated. Column chromatography (SiO2, AcOEt/MeOH/Et3N=70/25/5) gave 4-[{(N-(2-amino-5-trifluoromethylbenzoyl)glycyl)amino}methyl ]piperidine (284 mg, 86%): ESI/MS m/e 359.0 (M++H, Cl16H21F3N4O2).

Provenance & Evidence