Hydrochloric Acid → N-[4-(3-methoxyamino-propyl)-phenyl]-acetamide

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-(4-acetamidophenyl)propanal (96 mg, 0.50 mmol), methoxy]amine hydrochloride (92 mg, 1.1 mmol), and pyridine (110 μL) in methanol (0.7 mL) is heated in a 70° C. oil bath for 18 hours and then allowed to cool to room temperature. Methanol (1 mL) is added and the mixture is cooled to 0° C. in an ice-water bath. Borane.pyridine complex (0.11 mL, 1.1 mmol) is added, followed by the dropwise addition of 10% aqueous hydrochloric acid. The mixture is allowed to warm to room temperature and then concentrated under reduced pressure. The residue is purified by reverse-phase HPLC to give N-[4-(3-methoxyamino-propyl)-phenyl]-acetamide.

Provenance & Evidence