Methylamine → HCID 10176377, compound

Temperature

100 °C

The 3-chloro-1-(6-methyl(3-pyridyloxy))propane (2.78 g, 18.3 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 (4×25 mL). The pH of the aqueous phase was raised to 7 with 10% NaOH solution and other impurities were extracted with ether (4×30 mL). The aqueous layer was basified to pH 11 with 10% NaOH solution and extracted with ether (4×50 mL). The combined ether extracts were dried (Na2SO4), filtered, and concentrated by rotary evaporation to a residue that was dried briefly under high vacuum to give 1.224 g (45.3%) 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 (4×25 mL)
6. temperatureThe pH of the aqueous phase was raised to 7 with 10% NaOH solution and other impurities
7. extractionwere extracted with ether (4×30 mL)
8. extractionextracted with ether (4×50 mL)
9. dry with materialThe combined ether 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-424df4fd0ed0408b94037075244a37a1

Source dataset

uspto-grants-2003_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06627648B1