Diisopropylcarbodiimide → 4-[[N-(3-bromo-4-methylbenzoyl)glycyl]aminomethyl]-1-(4-chlorobenzyl)piperidine

Participants

Reaction Steps

3-Bromo-4-methylbenzoic acid (0.060 mmol), diisopropylcarbodiimide (0.060 mmol) and HOBt (0.060 mmol) were added to a solution of 1-(4-chlorobenzyl)-4-[(glycylamino)methyl]piperidine (0.050 mmol) in chloroform (1.35 mL) and tert-butanol (0.15 mL). The resulting reaction mixture was stirred at room temperature for 15 hours. The mixture was then loaded onto a Varian™ SCX column and washed with methanol/chloroform=1:1 (12 mL) and methanol (12 mL). The obtained crude product was eluted with a 2 M methanol solution of NH3 (5 mL) and concentrated to thereby afford 4-[[N-(3-bromo-4-methylbenzoyl)glycyl]aminomethyl]-1-(4-chlorobenzyl)piperidine (Compd. No. 1113) (16.1 mg, 65%). The purity was determined by RPLC/MS (95%). ESI/MS m/e 494.0 (C23H27BrClN3O2).

Provenance & Evidence