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

HRID 861174Notes

Reaction equation

HRID 861174 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, 8.24 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-fcc2c81120bc4bc3a25905bd100d0f67
Source dataset
uspto-grants-2006_12
Patent number
US07154737B2

Reaction notes

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