N-Methylbenzylamine → 8-(N-Benzyl-N-methylamino)octan-1-ol

Temperature

35 °C

8-Bromo-1-octanol (25 g, 119.6 mmol) in acetonitrile (50 mL) was added to a stirred solution of N-benzyl-N-methylamine (43.49 g, 358.9 mmol) and potassium carbonate (49.52 g, 358.9 mmol) in acetonitrile (250 mL) at 35° C. The reaction mixture was then stirred at 35° C. for 7 h and then cooled to ambient temperature. The potassium carbonate was filtered and the filtrate was concentrated under reduced pressure. The crude residue was dissolved in MTBE (400 mL) and the organic phase was washed with water, brine and dried over magnesium sulfate. N-methyl-2-pyrrolidone was added and the mixture was concentrated under reduced pressure to remove excess N-benzyl-N-methylamine. MTBE (400 mL) was added and the organic phase was washed with water, brine, and dried over magnesium sulfate, filtered and concentrated under reduced pressure to afford the title intermediate as an oil (˜100% conversion).

1. temperaturecooled to ambient temperature
2. filtrationThe potassium carbonate was filtered
3. concentrationthe filtrate was concentrated under reduced pressure
4. dissolutionThe crude residue was dissolved in MTBE (400 mL)
5. washthe organic phase was washed with water, brine
6. dry with materialdried over magnesium sulfate
7. additionN-methyl-2-pyrrolidone was added
8. concentrationthe mixture was concentrated under reduced pressure
9. customto remove excess N-benzyl-N-methylamine
10. additionMTBE (400 mL) was added
11. washthe organic phase was washed with water, brine
12. dry with materialdried over magnesium sulfate
13. filtrationfiltered
14. concentrationconcentrated under reduced pressure

ORD record

ord-a1e3462f223d48afb91079ab5a01fbba

Source dataset

uspto-grants-2007_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07183292B2