Diethyl Ether → N-(3-octadecanoyloxypropyl)-N,N-dimethyloctadecanaminium bromide

HRID 65564

Reaktionsgleichung

Reaktionsgleichung von HRID 65564
[C:1](Cl)(=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[CH3:21][N:22]([CH3:27])[CH2:23][CH2:24][CH2:25]O.[Br:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46].C([O:49]CC)C>>[Br-:28].[C:1]([O:19][CH2:25][CH2:24][CH2:23][N+:22]([CH3:27])([CH3:21])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46])(=[O:49])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Komponenten

5

Edukt 4

HCID 3283Diethyl Ether2×HCID 8212Stearoyl chlorideHCID 82181-BromooctadecaneHCID 766463-(Dimethylamino)-1-propanol

Produkt 1

HCID 22757060N-(3-octadecanoyloxypropyl)-N,N-dimethyloctadecanaminium bromide

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

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.

Aufarbeitung

  1. filtrationthe reaction mixture was filtered
  2. customthe solid recrystallized from ethyl acetate
  3. customrecrystallized from acetonitrile
  4. washAfter washing with ethyl ether
  5. customto remove any unreacted material the product
  6. customwas recrystallized from ethyl alcohol
  7. washwashed with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-7c103829d3a646d2a4191b05b82a94e1
Quelldatensatz
uspto-grants-1978_12
Patentnummer
US04128485

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