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

HRID 1395574Notes

Reaction equation

HRID 1395574 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 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 three 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-9bf4633557fd412daf38bcc1e87b058d
Source dataset
uspto-grants-1980_05
Patent number
US04204065

Reaction notes

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