Formaldehyde → HCID 18426185, compound

Participants

Reaction Steps

Sodium cyanoborohydride (26 mg, 0.42 mmol) and acetic acid (14 mL) were added to a mixture of 4-[N-(2-amino-5-bromobenzoyl)glycyl]aminomethyl-1-(4-chlorobenzyl)piperidine (Compd. No. 1042) (67 mg, 0.14 mmol) with a 37% aqueous solution of formaldehyde (0.112 mL, 1.4 mmol), acetonitrile (2 mL) and methanol (1.5 mL), and the resulting mixture was stirred at 50° C. for 30 hours. A 1 M aqueous solution of NaOH and dichloromethane were added to the mixture. The aqueous layer was separated, and the organic layer was dried over K2CO3, filtered, concentrated and purified by column chromatography (SiO2, 20% methanol/ethyl acetate) to afford 4-[N-[5-bromo-2-(dimethylamino)benzoyl]glycyl]aminomethyl-1-(4-chlorobenzyl)piperidine (Compd. No. 1428) (60 mg, 82%). The purity was determined by RPLC/MS (100%). ESI/MS m/e 523 (M++H, C24H30BrClF6N4O2).

Provenance & Evidence