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

HRID 1088562Notes

Reaction equation

HRID 1088562 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-dd7d94056c554f6c9ba57702b4941e96
Source dataset
uspto-grants-1990_10
Patent number
US04962096

Reaction notes

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