Ethanol → HCID 18426271, compound

Participants

Reaction Conditions

Reaction Steps

A triethyl orthoformate (6.5 mL) solution of 4-[N-(2-amino-5-bromobenzoyl)glycyl]aminomethyl-1-(4-chlorobenzyl)piperidine (Compd. No. 1042) (50 mg, 0.10 mmol) was stirred at 150° C. for 17 hours and concentrated to thereby provide a yellow solid. Sodium borohydride (7.6 mg, 0.2 mmol) was added to an ethanol (3 mL) solution of the yellow solid, and the mixture was stirred at room temperature for 14 hours. The resulting white precipitate was dissolved in dichloromethane, and the obtained solution was washed with a 1 M aqueous solution of NaOH (2 mL). The organic layer was separated, dried over K2CO3, filtered and concentrated, and the obtained crude product was purified by column chromatography (SiO2, 20% methanol/chloroform) to provide 4-[N-[5-bromo-2-(methylamino)benzoyl]glycyl]aminomethyl-1-(4-chlorobenzyl)piperidine (Compd. No. 1427) (40 mg, 80%). The purity was determined by RPLC/MS (100%). ESI/MS m/e 505 (M++H, C23H28BrClF6N4O2).

Provenance & Evidence