Hydrochloric Acid → (3-(5-Chloro(3-pyridyloxy))-1-methylpropyl)methylamine

Temperature

100 °C

Crude 3-bromo-1-(5-chloro(3-pyridyloxy)butane (1.50 g, 5.67 mmol) from the previous step was dissolved in methanol (10 mL) and added to a 40 wt % aqueous solution of methylamine (40 mL) in a heavy-walled glass pressure-tube apparatus. The mixture was stirred and heated at 100° C. (oil bath temperature) for 14 h. After cooling, the mixture was concentrated by rotary evaporation, and the product was extracted with chloroform (3×100 mL). The combined chloroform extracts were dried (Na2SO4), filtered, and concentrated by rotary evaporation to give a pale-brown oil. The product was dissolved in cold, 15% aqueous HCl (15 mL), stirred at 0° C. for 45 min and extracted with chloroform (50 mL). The aqueous layer was cooled to 0° C., basified with 15% aqueous NaOH solution to pH 8-9 and extracted with chloroform (3×75 mL). The combined extracts were dried (Na2SO4), filtered and concentrated by rotary evaporation to give 0.929 g (76.6%) of a pale-yellow oil.

1. temperatureAfter cooling
2. concentrationthe mixture was concentrated by rotary evaporation
3. extractionthe product was extracted with chloroform (3×100 mL)
4. dry with materialThe combined chloroform extracts were dried (Na2SO4)
5. filtrationfiltered
6. concentrationconcentrated by rotary evaporation
7. customto give a pale-brown oil
8. stirringstirred at 0° C. for 45 min
9. extractionextracted with chloroform (50 mL)
10. temperatureThe aqueous layer was cooled to 0° C.
11. extractionextracted with chloroform (3×75 mL)
12. dry with materialThe combined extracts were dried (Na2SO4)
13. filtrationfiltered
14. concentrationconcentrated by rotary evaporation

ORD record

ord-575e050c9841437385892751f22b04a3

Source dataset

uspto-grants-2003_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06627648B1