Methyl iodide → N,N-Diethyl-2-methoxy-N-methylethan-1-aminium iodide

HRID 1375296Notes

Reaction equation

HRID 1375296 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][N:5]([CH2:8][CH3:9])[CH2:6][CH3:7].[CH3:10][I:11]>O1CCCC1>[I-:11].[CH3:1][O:2][CH2:3][CH2:4][N+:5]([CH2:8][CH3:9])([CH2:6][CH3:7])[CH3:10]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 113555002-methoxyethyldiethylamine

Product 1

HCID 71374868N,N-Diethyl-2-methoxy-N-methylethan-1-aminium iodide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Next, 8.2 g of the 2-methoxyethyldiethylamine was dissolved in 10 ml of tetrahydrofuran (Wako Pure Chemical Industries), then 4.0 ml of methyl iodide (Wako Pure Chemical Industries) was added under ice cooling. After 30 minutes, the mixture was removed from the ice bath and stirred overnight at room temperature. The solvent in this reaction solution was subsequently driven off by vacuum distillation, and the resulting solids were recrystallized from an ethanol (Wako Pure Chemical Industries)—tetrahydrofuran system, yielding 16 g of 2-methoxyethyldiethylmethylammonium iodide.

Workup

  1. customthe mixture was removed from the ice bath
  2. distillationThe solvent in this reaction solution was subsequently driven off by vacuum distillation
  3. customthe resulting solids were recrystallized from an ethanol (Wako Pure Chemical Industries)—tetrahydrofuran system

Sources & evidence

ORD record
ord-7e491a2f420843178adf8dd7a970246f
Source dataset
uspto-grants-2007_01
Patent number
US07167353B2

Reaction notes

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