Sulfuric Acid → 4-(6-Fluoro-3,4-dimethoxyphenyl)-1,2,3,4-tetrahydroisoquinoline

HRID 1089810Notes

Reaction equation

HRID 1089810 reaction equation
[CH2:1]([NH:8][CH2:9][CH:10](O)[C:11]1[C:16]([F:17])=[CH:15][C:14]([O:18][CH3:19])=[C:13]([O:20][CH3:21])[CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(=O)(=O)(O)O.C([O-])(=O)C.[Na+]>FC(F)(F)C(O)=O>[F:17][C:16]1[C:11]([CH:10]2[C:7]3[C:2](=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH2:1][NH:8][CH2:9]2)=[CH:12][C:13]([O:20][CH3:21])=[C:14]([O:18][CH3:19])[CH:15]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 517045Sodium AcetateHCID 14719572HCID 14719572, compound

Product 1

HCID 199597124-(6-Fluoro-3,4-dimethoxyphenyl)-1,2,3,4-tetrahydroisoquinolineYield 100.3%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

α-[(benzylamino)methyl]-6-fluoro-3,4-dimethoxybenzyl alcohol (1.25 g) was dissolved in 8.75 ml of trifluoroacetic acid, and after adding thereto 0.37 ml of conc. sulfuric acid under ice-cooling, the mixture was stirred for 70 minutes. Then, 1.07 g of sodium acetate was added to the mixture, and the reaction mixture was concentrated. To the residue was added chloroform and water, and the mixture was basified by addition of conc. aqueous ammonia under ice-cooling. By a separating procedure, the chloroform layer was collected, washed with saturated aqueous NaCl solution, and dried over anhydrous sodium sulfate. The solvent was removed by distillation, giving 1.18 g of 4-(6-fluoro-3,4-dimethoxyphenyl)-1,2,3,4-tetrahydroisoquinoline as a syrupy matter.

Workup

  1. additionafter adding
  2. concentrationthe reaction mixture was concentrated
  3. additionTo the residue was added chloroform and water
  4. additionthe mixture was basified by addition of conc. aqueous ammonia under ice-
  5. temperaturecooling
  6. customBy a separating procedure, the chloroform layer was collected
  7. washwashed with saturated aqueous NaCl solution
  8. dry with materialdried over anhydrous sodium sulfate
  9. customThe solvent was removed by distillation

Sources & evidence

ORD record
ord-dc6a8dde9eff4d279c418e726ed76ead
Source dataset
uspto-grants-1992_01
Patent number
US05079256

Reaction notes

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