Methyl p-toluenesulfonate → 1,1-Dimethyl-2-hydroxymethylpyrrolidinium p-toluenesulfonate

HRID 2081492Notes

Reaction equation

HRID 2081492 reaction equation
[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][CH:3]1[CH2:7][OH:8].[C:9]1([CH3:20])[CH:14]=[CH:13][C:12]([S:15]([O:18]C)(=[O:17])=[O:16])=[CH:11][CH:10]=1>CC(C)=O>[C:9]1([CH3:20])[CH:10]=[CH:11][C:12]([S:15]([O-:18])(=[O:16])=[O:17])=[CH:13][CH:14]=1.[CH3:1][N+:2]1([CH3:9])[CH2:6][CH2:5][CH2:4][CH:3]1[CH2:7][OH:8]

Participants

4

Reactant 2

HCID 6645Methyl p-toluenesulfonateHCID 978361-Methyl-2-pyrrolidinemethanol

Product 1

HCID 150521731,1-Dimethyl-2-hydroxymethylpyrrolidinium p-toluenesulfonateYield 138.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

In 10 ml of acetone was dissolved 1.47 g of 1-methyl-2-pyrrolidinemethanol, and 2.38 g of methyl p-toluenesulfonate was added dropwise to the resulting solution. The mixture was stirred at room temperature, heated under reflux, and cooled to precipitate crystals. The crystals were collected by filtration and dried to give 2.67 g of the desired compound.

Workup

  1. additionwas added dropwise to the resulting solution
  2. temperatureheated
  3. temperatureunder reflux
  4. temperaturecooled
  5. customto precipitate crystals
  6. filtrationThe crystals were collected by filtration
  7. customdried

Sources & evidence

ORD record
ord-7617ba2dc89746a0b6ec9296f0a75fd0
Source dataset
uspto-grants-1993_02
Patent number
US05183811

Reaction notes

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