Reaktion #93842

Reaktionsgleichung

octadecanoylchloride

3-dimethylamino-1-propanol

ethyl ether

ethyl ether

1-bromooctadecane

→

N-(3-octadecanoyloxypropyl)-N,N-dimethyloctadecanaminium bromide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Filtrationthe reaction mixture was filtered
2. 2
   Sonstigethe solid recrystallized from ethyl acetate
3. 3
   Sonstigerecrystallized from acetonitrile
4. 4
   WaschenAfter washing with ethyl ether
5. 5
   Sonstigeto remove any unreacted material the product
6. 6
   Sonstigewas recrystallized from ethyl alcohol
7. 7
   Waschenwashed with ethyl acetate

Vorschrift

To a solution of 0.2 mole octadecanoylchloride in 400 ml ethyl ether was added a solution of 32 g (0.31 mole) 3-dimethylamino-1-propanol in 50 ml ethyl ether. After stirring about 2 hours, the reaction mixture was filtered and the solid recrystallized from ethyl acetate. It was converted to the free base, 3-dimethylaminopropyl octadecanoate, with sodium hydroxide and recrystallized from acetonitrile. A mixture of 18.3 g (0.049 mole) of this amine and 16.2 g (0.049 mole) of 1-bromooctadecane was heated in an oven at 100° C. for 7 hours. After washing with ethyl ether to remove any unreacted material the product was recrystallized from ethyl alcohol and washed with ethyl acetate.

Quelle