Hippuric Acid → 4-[(N-benzoylglycyl)amino]methyl-1-(4-chlorobenzyl)piperidine

Participants

Reaction Conditions

Reaction Steps

A solution of 4-(aminomethyl)-1-(4-chlorobenzyl)piperidine (50 mg, 0.21 mmol) in CH2Cl3 (1 mL) was treated with hippuric acid (38 mg, 0.21 mmol), EDCI (48 mg, 0.24 mmol), HOBt (31 mg, 0.23 mmol) and Et3N (38 μL, 0.27 mmol). The reaction mixture was stirred for 16 h at 25° C., diluted with 1 mL of CH2Cl2, washed with 2 N aqueous NaOH solution (2×0.75 mL), dried (MgSO4) and concentrated. Chromatography (SiO2, 6 to 8% CH3OH/CH3Cl2 gradient elution) afforded 4-{(N-benzoylglycyl)amino}methyl-1-(4-chlorobenzyl)piperidine (compound No. 458) which was treated with TFA to give a TFA salt (105 mg, 97%): The purity was determined by RPLC/MS (85%); ESI/MS m/e 400 (M++H, C22H26ClN3O2).

Provenance & Evidence