Methyl iodide → 2-(4-Chlorobenzyl)-1,1-dimethylpyrrolidinium iodide

HRID 1278066Notes

Reaction equation

HRID 1278066 reaction equation
[CH3:1][I:2].[Cl:3][C:4]1[CH:16]=[CH:15][C:7]([CH2:8][CH:9]2[CH2:13][CH2:12][CH2:11][N:10]2[CH3:14])=[CH:6][CH:5]=1>CC(C)=O>[I-:2].[Cl:3][C:4]1[CH:16]=[CH:15][C:7]([CH2:8][CH:9]2[CH2:13][CH2:12][CH2:11][N+:10]2([CH3:1])[CH3:14])=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 234525052-[(4-Chlorophenyl)methyl]-1-methylpyrrolidine

Product 1

HCID 234525842-(4-Chlorobenzyl)-1,1-dimethylpyrrolidinium iodide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Add 3.72 g of methyl iodide dropwise, with stirring, to 5.5 g of 2-(4-chlorobenzyl)-1-methylpyrrolidine in 40 ml of acetone. Filter off the formed crystalline precipitate and recrystallize it twice from methanol/diethyl ether to obtain 6.9 g (75% of theory) of the title compound (m.p. 184° to 186°).

Workup

  1. filtrationFilter off the formed crystalline precipitate
  2. customrecrystallize it twice from methanol/diethyl ether

Sources & evidence

ORD record
ord-2a9000da7c0b47b48600caabb4867034
Source dataset
uspto-grants-1981_07
Patent number
US04279918

Reaction notes

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