Methylamine → N-methyl-2-(pyridin-3-yloxy)ethanamine

Temperature

100 °C

The 2-chloro-1-(3-pyridyloxy)ethane (2.17 g, 13.8 mmol) was dissolved in methanol (25 mL) and added to a 40 wt % aqueous solution of methylamine (50 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 was adjusted to 1 with 10% HCl solution and impurities were extracted with chloroform (2×50 mL). The pH of the aqueous phase was raised to 6 with 10% NaOH solution and other impurities were extracted with ether (3×25 mL). The aqueous layer was basified to pH 10 with 10% NaOH solution and extracted with chloroform (4×50 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 0.253 g (12.0%) 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 chloroform (2×50 mL)
6. temperatureThe pH of the aqueous phase was raised to 6 with 10% NaOH solution and other impurities
7. extractionwere extracted with ether (3×25 mL)
8. extractionextracted with chloroform (4×50 mL)
9. dry with materialThe combined chloroform extracts were dried (Na2SO4)
10. filtrationfiltered
11. concentrationconcentrated by rotary evaporation to a residue that
12. customwas dried briefly under high vacuum

ORD record

ord-ce474a07b9a84ee6864692caa6e7707d

Source dataset

uspto-grants-2003_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06627648B1