Methyl iodide → 1H-Pyrrole-2-methanaminium, N,N,N-trimethyl-, iodide (1:1)

HRID 1253027Notes

Reaction equation

HRID 1253027 reaction equation
[CH3:1][I:2].[CH3:3][N:4]([CH2:6][C:7]1[NH:8][CH:9]=[CH:10][CH:11]=1)[CH3:5]>CCOCC>[I-:2].[NH:8]1[CH:9]=[CH:10][CH:11]=[C:7]1[CH2:6][N+:4]([CH3:1])([CH3:5])[CH3:3]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 260796N,N-dimethyl-1-(1H-pyrrol-2-yl)methanamine

Product 1

HCID 139751381H-Pyrrole-2-methanaminium, N,N,N-trimethyl-, iodide (1:1)

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a cold solution of 67 g (0.47 mole) of methyliodide in 150 ml of anhydrous ether was added slowly a dry ether solution of 50 gm of 2-(N,N-dimethylaminomethyl)pyrrole (0.37 mole). A white solid begain to precipitate out of solution. The mixture was heated to 30° for 1.5 hours, filtered and washed with 2/×30 ml of ether to obtain 59 gm of 2-pyrryl)methyltrimethylammonium iodide which was used in the next step without further purification.

Workup

  1. customA white solid begain to precipitate out of solution
  2. temperatureThe mixture was heated to 30° for 1.5 hours
  3. filtrationfiltered
  4. washwashed with 2/×30 ml of ether
  5. customto obtain 59 gm of 2-pyrryl)methyltrimethylammonium iodide which
  6. customwas used in the next step without further purification

Sources & evidence

ORD record
ord-c27057f2bf954469bd09079bd76b3332
Source dataset
uspto-grants-1988_05
Patent number
US04746669

Reaction notes

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