Hydroxyamine hydrochloride → HCID 23084750, compound

Participants

Reaction Steps

A mixture (1:1, 17.5 g) of α-(1-ethoxycarbonylpiperidin-4-yl)carbonylphenylacetonitrile and α-(1-methoxycarbonylpiperidin-4-yl)carbonylphenylacetonitrile, hydroxylamine hydrochloride (5.63 g) and sodium acetate (13.1 g) were suspended in water (20 mL) and ethanol (160 mL), and the suspension was heated under reflux for 6 hrs. After the completion of the reaction, the mixture was cooled to room temperature. The insoluble material was filtered off using ethanol, and the filtrate was concentrated under reduced pressure. The residue was dissolved in chloroform, and washed with water and saturated brine. The chloroform layer was concentrated under reduced pressure, and the obtained crystals were purified by column chromatography (n-hexane:ethyl acetate=3:1→1:1) to give a mixture (1:1, 7.02 g) of 5-amino-3-(1-ethoxycarbonylpiperidin-4-yl)-4-phenylisoxazole and 5-amino-3-(1-methoxycarbonylpiperidin-4-yl)-4-phenylisoxazole as pale-yellow crystals.

Provenance & Evidence