Methyl iodide → N,N,N-Trimethyl(1-methyl-1H-pyrrol-2-yl)methanaminium iodide

HRID 1269411Notes

Reaction equation

HRID 1269411 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[N:6]([CH3:10])[CH:7]=[CH:8][CH:9]=1)[CH3:3].C[I:12].[C:13](OCC)(=O)C>C(O)C>[I-:12].[CH3:10][N:6]1[CH:7]=[CH:8][CH:9]=[C:5]1[CH2:4][N+:2]([CH3:13])([CH3:3])[CH3:1]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 920231H-Pyrrole-2-methanamine, N,N,1-trimethyl-

Product 1

HCID 12346658N,N,N-Trimethyl(1-methyl-1H-pyrrol-2-yl)methanaminium iodideYield 91%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Subsequently, to absolution of 2-(N,N-dimethylaminomethyl)-1-methylpyrrole (30.00 g, 217.5 mmol) obtained above in ethanol (220 ml) was added methyl iodide (16.2 ml, 260–2 mmol) with stirring under ice-cooling, and then the resulting mixture was stirred at room temperature for 2 hours. After stirring, ethyl acetate (220 ml) was added to the reaction mixture. The crystals precipitated were collected by filtration, washed with ethyl acetate and dried to afford (1-methylpyrrol-2-yl)methyl trimethylammonium iodide (55.34 g, yield: 91%).

Workup

  1. temperaturecooling
  2. stirringthe resulting mixture was stirred at room temperature for 2 hours
  3. stirringAfter stirring
  4. customThe crystals precipitated
  5. filtrationwere collected by filtration
  6. washwashed with ethyl acetate
  7. customdried

Sources & evidence

ORD record
ord-fa228b168167493195695c92fd371ace
Source dataset
uspto-grants-2007_04
Patent number
US07199150B2

Reaction notes

Loading…