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

HRID 1724612Notes

Reaction equation

HRID 1724612 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, 41.2 g of the 2-methoxyethyldiethylamine was dissolved in 300 mL of tetrahydrofuran (Wako Pure Chemical Industries, Inc.), following which 20.0 mL of methyl iodide (Wako Pure Chemical Industries) was added under ice cooling. After 30 minutes, the ice bath was removed and stirring was carried out overnight at room temperature. The solvent in this reaction solution was driven off by vacuum distillation, and the resulting solids were recrystallized from an ethanol (Wako Pure Chemical Industries)—tetrahydrofuran mixture, yielding 80 g of 2-methoxyethyldiethylmethylammonium iodide.

Workup

  1. additionwas added under ice cooling
  2. customthe ice bath was removed
  3. waitwas carried out overnight at room temperature
  4. distillationThe solvent in this reaction solution was driven off by vacuum distillation
  5. customthe resulting solids were recrystallized from an ethanol (Wako Pure Chemical Industries)—tetrahydrofuran mixture

Sources & evidence

ORD record
ord-6c30327a03604611a010dad45a74cf48
Source dataset
uspto-grants-2009_02
Patent number
US07488425B2

Reaction notes

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