Trimethylamine → Benzenemethanaminium, N,N,N,4-tetramethyl-, chloride (1:1)

HRID 1883642Notes

Reaction equation

HRID 1883642 reaction equation
[C:1]1([C:7]2[CH:14]=[CH:13][C:10]([CH2:11][Cl:12])=[CH:9][CH:8]=2)C=CC=CC=1.[CH3:15][N:16]([CH3:18])[CH3:17]>C1(C)C=CC=CC=1>[Cl-:12].[CH3:1][C:7]1[CH:14]=[CH:13][C:10]([CH2:11][N+:16]([CH3:18])([CH3:17])[CH3:15])=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 1146TrimethylamineHCID 154634-Phenylbenzyl chloride

Product 1

HCID 12383100Benzenemethanaminium, N,N,N,4-tetramethyl-, chloride (1:1)

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 3.0 g (14.8 mmol) of 4-phenylbenzyl chloride, 10 ml of toluene and 5.6 ml (26.6 mmol) of a 30 wt % trimethylamine aqueous solution was stirred for 3.7 hours at 60° C. The reaction solution was separated, and the resulted aqueous layer was washed with t-butyl methyl ether. The aqueous layer was filtrated through celite, and the filtrate was concentrated to obtain 4.07 g of (4-methylbenzyl)-trimethylammonium chloride having a melting point of 204.8° C.

Workup

  1. customThe reaction solution was separated
  2. washthe resulted aqueous layer was washed with t-butyl methyl ether
  3. filtrationThe aqueous layer was filtrated through celite
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-fbfa12436d10482cb48cfd5176021ebc
Source dataset
uspto-grants-2004_07
Patent number
US06762197B2

Reaction notes

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