Triethylamine → N-[(Dodecanoyloxy)methyl]-N,N-diethylethanaminium chloride

HRID 1446791Notes

Reaction equation

HRID 1446791 reaction equation
[C:1]([O:14][CH2:15][Cl:16])(=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[CH2:17]([N:19]([CH2:22][CH3:23])[CH2:20][CH3:21])[CH3:18]>CCOCC>[Cl-:16].[C:1]([O:14][CH2:15][N+:19]([CH2:22][CH3:23])([CH2:20][CH3:21])[CH2:17][CH3:18])(=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 543634Chloromethyl dodecanoate

Product 1

HCID 20552717N-[(Dodecanoyloxy)methyl]-N,N-diethylethanaminium chloride

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

2.49 g (0.01 mol) chloromethyl n-dodecanoate (1b) and 1.01 g (0.01 mol) triethylamine were mixed and heated together at 90° for three hr. On cooling to room temperature, anhydrous ether was added to the mixture and the mixture was triturated in ahydrous ether overnight. The solid was isolated by filtration under a nitrogen atmosphere and thoroughly washed with ether. After drying in vacuo over calcium sulfate at room temperature 0.6 g (0.002 mol 20%, 2h was obtained as a hygroscopic solid, mp 72°-77°.

Workup

  1. temperatureheated together at 90° for three hr
  2. customthe mixture was triturated in ahydrous ether overnight
  3. customThe solid was isolated by filtration under a nitrogen atmosphere
  4. washthoroughly washed with ether
  5. dry with materialAfter drying in vacuo over calcium sulfate at room temperature 0.6 g (0.002 mol 20%

Sources & evidence

ORD record
ord-68afcd2d1627473db8ee285f2649d75e
Source dataset
uspto-grants-1982_02
Patent number
US04313889

Reaction notes

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