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

Temperatur

80 °C

From 8-Chlorooctan-1-ol: A 2-L flask was charged with benzylmethylamine (270 g, 2.23 mol), sodium carbonate (157 g, 1.48 mol), sodium iodide (11.1 g, 0.074 mol), 8-chlorooctanol (122 g, 0.74 mol) and acetonitrile (1000 mL) and the resulting suspension was stirred at 80° C. for 20–30 h. The reaction mixture was then concentrated to a volume of about 500 mL and water (600 mL) and tert-butyl methyl ether (1000 mL) were added. The MTBE layer was then separated and washed with water (500 mL). The MTBE solution was concentrated by distillation under vacuum to provide an oil and the oil was then further concentrated by distillation under high vacuum to remove excess benzylmethylamine. N-methyl-2-pyrrolidone (300 mL) was then added to the remaining oil and this solution concentrated by distillation under high vacuum to provide an oil. The oil was dissolved in MTBE (1000 mL) and the resulting solution was washed with water (2×500 mL), brine (500 mL), dried with sodium sulfate (100 g), filtered and concentrated by distillation to afford the title compound as an oil (178 g, 96% yield, >95% purity).

1. concentrationThe reaction mixture was then concentrated to a volume of about 500 mL and water (600 mL) and tert-butyl methyl ether (1000 mL)
2. additionwere added
3. customThe MTBE layer was then separated
4. washwashed with water (500 mL)
5. concentrationThe MTBE solution was concentrated by distillation under vacuum
6. customto provide an oil
7. concentrationthe oil was then further concentrated by distillation under high vacuum
8. customto remove excess benzylmethylamine
9. additionN-methyl-2-pyrrolidone (300 mL) was then added to the remaining oil
10. concentrationthis solution concentrated by distillation under high vacuum
11. customto provide an oil
12. washthe resulting solution was washed with water (2×500 mL), brine (500 mL)
13. dry with materialdried with sodium sulfate (100 g)
14. filtrationfiltered
15. concentrationconcentrated by distillation

ORD-Eintrag

ord-2396a5983d5a474c8730bd84baf2517b

Quelldatensatz

uspto-grants-2007_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07183292B2