Hydrochloric Acid → HCID 67615506, compound

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).

1. temperaturecooled to 0° under nitrogen
2. additionwas added dropwise
3. stirringthe mixture was stirred at room temperature for 18 h
4. temperaturethe mixture was heated
5. temperatureto reflux for 3 h
6. customThe mixture was evaporated in vacuo
7. customthe residue was partitioned between 0.88 ammonia (40 ml ) in water (200 ml) and chloroform (100 ml)
8. extractionThe aqueous phase was extracted with chloroform (100 ml×3)
9. dry with materialThe combined organic extracts were dried (Na2SO4)
10. customevaporated to an oil
11. dissolutionThis was dissolved in ethanol (50 ml)
12. additionby adding ethereal hydrogen chloride
13. customThe solution was evaporated
14. customthe residue recrystallised from i-propanol-hexane
15. customto give a white solid
16. extractionextracted with dichloromethane (200 ml×3)
17. dry with materialThe combined organic extracts were dried (Na2SO4)
18. customevaporated in vacuo

ORD record

ord-0edbb30235bd4cbd9fff348039869a2c

Source dataset

uspto-grants-1998_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05843966