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

HRID 1593346Notes

Reaction equation

HRID 1593346 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), following which 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 the resulting reaction mixture was then 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. additionwas added under ice cooling
  2. customthe mixture was removed from the ice bath
  3. customThe solvent in the resulting reaction mixture
  4. distillationwas then driven off by vacuum distillation
  5. customthe resulting solids were recrystallized from an ethanol (Wako Pure Chemical Industries)-tetrahydrofuran system

Sources & evidence

ORD record
ord-c874a9245ca94705b04cdafbe3025f31
Source dataset
uspto-grants-2007_11
Patent number
US07297289B2

Reaction notes

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