Hydrochloric Acid → HCID 67615506, compound

Participants

Reaction Steps

Dry tetrahydrofuran (100 ml) was added to a flask containing zirconium (IV) chloride (6.17 g) cooled to 0° under nitrogen. Sodium borohydride (4.0 g) was added and the mixture stirred as it warmed to room temperature over 15 mins. A suspension of 6-(3bromo-phenyl)-piperidin-2,5dione 5-oxime (xg) in dry tetrahydrofuran (50 ml) was added dropwise and the mixture was stirred at room temperature for 18 h. Concentrated hydrochloric acid (10 ml) in methanol (60 ml) was cautiously added and the mixture was heated to reflux for 3 h. The mixture was evaporated in vacuo and the residue was partitioned between 0.88 ammonia (40 ml ) in water (200 ml) and chloroform (100 ml). The aqueous phase was extracted with chloroform (100 ml×3). The combined organic extracts were dried (Na2SO4) and evaporated to an oil. This was dissolved in ethanol (50 ml) and acidified by adding ethereal hydrogen chloride. The solution was evaporated and the residue recrystallised from i-propanol-hexane to give a white solid. The solid was treated with 2N sodium hydroxide solution (200 ml) and extracted with dichloromethane (200 ml×3). The combined organic extracts were dried (Na2SO4) and evaporated in vacuo to give the title compound as a yellow-brown oil (1.10 g).

Provenance & Evidence