Formaldehyde → HCID 18426185, compound

Participants

Reaction Conditions

Reaction Steps

Sodium cyanoborohydride (26 mg, 0.42 mmol) and acetic acid (14 μL) was added successively to a mixture of 4-{N-(2-amino-5-bromobenzoyl)glycyl}aminomethyl-1-(4-chlorobenzyl)piperidine (Compound No. 1042) (67 mg, 0.14 mmol), 37% formaldehyde solution in water (0.112 mL, 1.4 mmol), acetonitrile (2 mL), and methanol (1.5 mL). After the solution was stirred at 50° C. for 30 h, 1 N aqueous NaOH and dichloromethane were added. The aqueous layer was separated and the organic layer was dried over K2CO3, filtered and evaporated. Column chromatography (SiO2, 20% MeOH/AcOEt) gave 4-[N-{5-bromo-2-(dimethylamino)benzoyl)glycyl}aminomethyl-1-(4-chlorobenzyl)piperidine (Compound No. 1428) (60 mg, 82%): The purity was determined by RPLC/MS (100%); ESI/MS m/e 523 (C24H30BrClF6N4O2).

Provenance & Evidence