Methylamine → HCID 9834297, compound

The crude (3-(3-chloropropoxy)phenyl)dimethylamine (4.06 g, 19.01 mmol) was dissolved in methanol (30 mL) and added to a 40 wt % aqueous solution of methylamine (75 mL) in a heavy-walled glass pressure-tube apparatus. The tube was sealed and the mixture was stirred at ambient temperature for 16 h, followed by heating at 87° C. (oil bath temperature) for 3 h. After cooling, the solution was concentrated by rotary evaporation to a lavender-brown semi-solid. Saturated NaCl solution (35 mL) was added. The mixture was acidified to pH 1 with 10% HCl solution and extracted with CHCl3 (5×30 mL) to remove impurities. The dark-brown aqueous layer was basified to pH 7 with 30% NaOH solution and extracted with ether (4×40 mL) to remove impurities. The brown aqueous layer was basified with 30% NaOH solution to pH 12 and extracted with ether (4×50 mL). The combined ether extracts were dried (Na2SO4), filtered and concentrated by rotary evaporation, producing an oil. The product was dried briefly under high vacuum to afford 2.24 g (56.6%) of a dark-brown oil.

1. customThe tube was sealed
2. temperatureby heating at 87° C. (oil bath temperature) for 3 h
3. temperatureAfter cooling
4. concentrationthe solution was concentrated by rotary evaporation to a lavender-brown semi-solid
5. additionSaturated NaCl solution (35 mL) was added
6. extractionextracted with CHCl3 (5×30 mL)
7. customto remove impurities
8. extractionextracted with ether (4×40 mL)
9. customto remove impurities
10. extractionextracted with ether (4×50 mL)
11. dry with materialThe combined ether extracts were dried (Na2SO4)
12. filtrationfiltered
13. concentrationconcentrated by rotary evaporation
14. customproducing an oil
15. customThe product was dried briefly under high vacuum

ORD record

ord-d1f2f2498ac347669560c78546c8210b

Source dataset

uspto-grants-2003_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06627648B1