Réaction #985354

Équation de réaction

8-Chlorooctan-1-ol

benzylmethylamine

sodium carbonate

sodium iodide

8-chlorooctanol

acetonitrile

→

title compound

Rendement 96.0%

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

Rendement 96.0%

Solvants

MTBE

Conditions de réaction

Traitement

1. 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. 2
   workup.ADDITIONwere added
3. 3
   AutreThe MTBE layer was then separated
4. 4
   Lavagewashed with water (500 mL)
5. 5
   ConcentrationThe MTBE solution was concentrated by distillation under vacuum
6. 6
   Autreto provide an oil
7. 7
   Concentrationthe oil was then further concentrated by distillation under high vacuum
8. 8
   Autreto remove excess benzylmethylamine
9. 9
   workup.ADDITIONN-methyl-2-pyrrolidone (300 mL) was then added to the remaining oil
10. 10
    Concentrationthis solution concentrated by distillation under high vacuum
11. 11
    Autreto provide an oil
12. 12
    Lavagethe resulting solution was washed with water (2×500 mL), brine (500 mL)
13. 13
    Séchagedried with sodium sulfate (100 g)
14. 14
    Filtrationfiltered
15. 15
    Concentrationconcentrated by distillation

Mode opératoire

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).

Source