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

HRID 1729707Notes

Reaction equation

HRID 1729707 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 3 hr. On cooling to room temperature, anhydrous ether was added to the mixture and the mixture was triturated in anhydrous ether overnite. 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 3 hr
  2. customthe mixture was triturated in anhydrous ether overnite
  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-5b3ee94a8f9b460bb7be9f72adcfd8f0
Source dataset
uspto-grants-1976_11
Patent number
US03989711

Reaction notes

Loading…