Ethanol → HCID 21094258, compound

A solution of 1-(3-pyridyl)-3-(4-oxanyl)propylamine (1.00 g, 4.54 mmol) in 48% aqueous HBr (15 mL) was saturated with HBr gas. The mixture was heated in a pressure tube at 100°–120° C. for 12 h. The tube was cooled in ice water and the contents transferred to a 250 mL round bottom flask. Removal of the volatiles by rotary evaporation afforded a light yellow solid. Absolute ethanol (200 mL) and solid K2CO3 (10 g) were added and the mixture was heated at reflux for 8 h. The mixture was filtered through a Celite plug, which was then washed with ethanol (25 mL). The combined filtrates were concentrated by rotary evaporation; the solid obtained was suspended in saturated aqueous NaCl (10 mL) and extracted with chloroform (4×30 mL). The combined organic extracts were dried (K2CO3), filtered and concentrated by rotary evaporation to give a dark brown oil. Short path distillation (120°–122° C., 2 mm) provided 0.750 g of the desired free base as a colorless oil (81.7% yield).

1. temperatureThe mixture was heated in a pressure tube at 100°–120° C. for 12 h
2. customthe contents transferred to a 250 mL round bottom flask
3. customRemoval of the volatiles
4. customby rotary evaporation
5. customafforded a light yellow solid
6. temperaturethe mixture was heated
7. temperatureat reflux for 8 h
8. filtrationThe mixture was filtered through a Celite plug, which
9. washwas then washed with ethanol (25 mL)
10. concentrationThe combined filtrates were concentrated by rotary evaporation
11. customthe solid obtained
12. extractionextracted with chloroform (4×30 mL)
13. dry with materialThe combined organic extracts were dried (K2CO3)
14. filtrationfiltered
15. concentrationconcentrated by rotary evaporation
16. customto give a dark brown oil
17. distillationShort path distillation (120°–122° C., 2 mm)

ORD record

ord-308efb69f6c54777b251736d58f17aaa

Source dataset

uspto-grants-2007_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07214686B2