Methyl p-toluenesulfonate → 2,2-Dimethyl-3-hydroxymethyl-1,2,3,4-tetrahydroisoquinolinium p-toluenesulfonate

HRID 2081498Notes

Reaction equation

HRID 2081498 reaction equation
[CH3:1][N:2]1[CH:11]([CH2:12][OH:13])[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3]1.[C:14]1([CH3:25])[CH:19]=[CH:18][C:17]([S:20]([O:23]C)(=[O:22])=[O:21])=[CH:16][CH:15]=1>CC(C)=O>[C:14]1([CH3:25])[CH:15]=[CH:16][C:17]([S:20]([O-:23])(=[O:21])=[O:22])=[CH:18][CH:19]=1.[CH3:1][N+:2]1([CH3:14])[CH:11]([CH2:12][OH:13])[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3]1

Participants

4

Reactant 2

HCID 6645Methyl p-toluenesulfonateHCID 589740(2-Methyl-1,2,3,4-tetrahydroisoquinolin-3-yl)methanol

Product 1

HCID 150522362,2-Dimethyl-3-hydroxymethyl-1,2,3,4-tetrahydroisoquinolinium p-toluenesulfonateYield 144%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

In 12 ml of acetone was dissolved 887 mg of 2-methyl -1,2,3,4-tetrahydro-3-isoquinolinemethanol, and 932 mg of methyl p-toluenesulfonate was added dropwise to the resulting solution. The mixture was stirred at room temperature for 3 hours to precipitate crystals. The crystals were collected by filtration, washed with acetone and dried under reduced pressure to give 1.31 g of the desired compound.

Workup

  1. additionwas added dropwise to the resulting solution
  2. customto precipitate crystals
  3. filtrationThe crystals were collected by filtration
  4. washwashed with acetone
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-da42e945887b41dbb884d6636e92d43c
Source dataset
uspto-grants-1993_02
Patent number
US05183811

Reaction notes

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