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

HRID 65564
Notes
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Reaction equation

HRID 65564 reaction equation
[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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 4

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

Product 1

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

Conditions

Temperature
100 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-7c103829d3a646d2a4191b05b82a94e1
Source dataset
uspto-grants-1978_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04128485

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes