Réaction #1218

Équation de réaction

benzylamine

1,2-epoxyoctadecane

→

title compound

Rendement 83.1%

1-amino-2-octadecanol

Rendement 83.1%

Conditions de réaction

Traitement

1. 1
   AutreA 500-ml flask equipped with a stirrer
2. 2
   workup.ADDITIONwere added dropwise over 3 hours
3. 3
   workup.STIRRINGStirring
4. 4
   workup.DISTILLATIONBenzyl alcohol was distilled off under reduced pressure
5. 5
   workup.ADDITIONthe residue was charged into a 500-ml autoclave, to which 300 ml of ethanol and 10 g of 5% Pd/C
6. 6
   workup.ADDITIONwere added
7. 7
   Autrefor 48 hours
8. 8
   Autreat room temperature
9. 9
   AutreAfter the catalyst was separated by filtration
10. 10
    Concentrationthe filtrate was concentrated under reduced pressure
11. 11
    Autrethe residue was recrystallized from hexane

Mode opératoire

A 500-ml flask equipped with a stirrer was charged with 160 g (1.5 mol) of benzylamine, to which 29 g (0.11 mol) of 1,2-epoxyoctadecane were added dropwise over 3 hours while stirring at 100° C. Stirring was conducted further for 12 hours at 100° C. Benzyl alcohol was distilled off under reduced pressure, and the residue was charged into a 500-ml autoclave, to which 300 ml of ethanol and 10 g of 5% Pd/C were added to conduct hydrogenolysis for 48 hours at room temperature under a hydrogen pressure of 5 atm. After the catalyst was separated by filtration, the filtrate was concentrated under reduced pressure, and the residue was recrystallized from hexane, thereby obtaining 26.1 g (yield: 83%) of the title compound (IIh-7).

Source