Methylamine → HCID 10176531, compound

Temperature

100 °C

Crude 5-(3-chloropropoxy)-3-methoxypyridine (0.75 g, 3.73 mmol) was dissolved in methanol (10.5 mL) and added to a 40 wt % aqueous solution of methylamine (10.6 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 solution was concentrated by rotary evaporation. Saturated NaCl solution (50 mL) was added, and the mixture was basified with 10% NaOH solution to pH 11. The mixture was extracted with ether (4×50 mL). The combined ether extracts were dried (MgSO4), filtered and concentrated by rotary evaporation to give 0.54 g of a brown oil. The product was purified by column chromatography on silica gel (18 g) eluting with CHCl3—CH3OH (1:1, v/v) to remove impurities, followed by CHCl3—CH3OH-Et3N (50:50:2, v/v/v) to collect the product. Selected fractions containing the product were combined and concentrated by rotary evaporation. The resulting brown oil was dissolved in CHCl3 (25 mL), dried (MgSO4), filtered, and concentrated by rotary evaporation to give 0.228 g (31.2%) of a brown oil.

1. customThe tube was sealed
2. temperatureAfter cooling
3. concentrationthe solution was concentrated by rotary evaporation
4. additionSaturated NaCl solution (50 mL) was added
5. extractionThe mixture was extracted with ether (4×50 mL)
6. dry with materialThe combined ether extracts were dried (MgSO4)
7. filtrationfiltered
8. concentrationconcentrated by rotary evaporation

ORD record

ord-73845735b8a2412a9f7133d3c9cadc00

Source dataset

uspto-grants-2003_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06627648B1