Ethylamine → Ethyl(3-(3-pyridyloxy)propyl)amine

Temperature

100 °C

The 3-chloro-1-(3-pyridyloxy)propane (1.00 g, 5.84 mmol) was dissolved in methanol (50 mL) and added to a 2.0 M solution of ethylamine in tetrahydrofuran (5 mL) in a heavy-walled glass pressure-tube apparatus. The tube was sealed and the mixture was stirred and heated at 100° C. (oil bath temperature) for 4 h. After cooling, the mixture was concentrated by rotary evaporation. Saturated NaCl solution (25 mL) was added to the residue. The pH of the solution was adjusted to 6, and impurities were extracted with ether (3×15 mL). The aqueous layer was basified to pH 10 with 10% NaOH solution and extracted with chloroform (4×15 mL). The combined chloroform extracts were dried (Na2SO4), filtered, and concentrated by rotary evaporation to a residue that was dried briefly under high vacuum to give 400 mg (38.1%) of an oil.

1. customThe tube was sealed
2. temperatureAfter cooling
3. concentrationthe mixture was concentrated by rotary evaporation
4. additionSaturated NaCl solution (25 mL) was added to the residue
5. extractionwere extracted with ether (3×15 mL)
6. extractionextracted with chloroform (4×15 mL)
7. dry with materialThe combined chloroform extracts were dried (Na2SO4)
8. filtrationfiltered
9. concentrationconcentrated by rotary evaporation to a residue that
10. customwas dried briefly under high vacuum

ORD record

ord-211aa002640c4eec816169928b6b0204

Source dataset

uspto-grants-2003_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06627648B1