Sulfuric Acid → 4-(6-Fluoro-3,4-dimethoxyphenyl)-7,8-dimethoxy-1,2,3,4-tetrahydroisoquinoline

HRID 54677Notes

Reaction equation

HRID 54677 reaction equation
[CH3:1][O:2][C:3]1[C:24]([O:25][CH3:26])=[CH:23][CH:22]=[CH:21][C:4]=1[CH2:5][NH:6][CH2:7][CH:8](O)[C:9]1[C:14]([F:15])=[CH:13][C:12]([O:16][CH3:17])=[C:11]([O:18][CH3:19])[CH:10]=1.S(=O)(=O)(O)O.C([O-])(=O)C.[Na+]>FC(F)(F)C(O)=O>[F:15][C:14]1[C:9]([CH:8]2[C:21]3[C:4](=[C:3]([O:2][CH3:1])[C:24]([O:25][CH3:26])=[CH:23][CH:22]=3)[CH2:5][NH:6][CH2:7]2)=[CH:10][C:11]([O:18][CH3:19])=[C:12]([O:16][CH3:17])[CH:13]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 517045Sodium AcetateHCID 14719568alpha-[[(2,3-Dimethoxybenzyl)amino]methyl]-6-fluoro-3,4-dimethoxybenzyl alcohol

Product 1

HCID 199597004-(6-Fluoro-3,4-dimethoxyphenyl)-7,8-dimethoxy-1,2,3,4-tetrahydroisoquinolineYield 98.9%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

α-[[(2,3-dimethoxybenzyl)amino]methyl]-6-fluoro-3,4-dimethoxybenzyl alcohol (1.0 g) was dissolved in 7 ml of trifluoroacetic acid, and after adding thereto under ice cooling, conc. sulfuric acid (0.25 ml), the mixture was stirred for 40 minutes. 0.72 g of sodium acetate was added to the reaction mixture, and the 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. After separating procedure, the chloroform layer was collected, washed with saturated aqueous NaCl solution, and dried over anhydrous sodium sulfate. The solvent was distilled off, 0.94 g of 4-(6-fluoro-3,4-dimethoxyphenyl)-7,8-dimethoxy-1,2,3,4-tetrahydroisoquinoline was obtained as a syrupy matter.

Workup

  1. additionafter adding
  2. concentrationthe 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 cooling
  5. customAfter separating procedure
  6. customthe chloroform layer was collected
  7. washwashed with saturated aqueous NaCl solution
  8. dry with materialdried over anhydrous sodium sulfate
  9. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-06f55568dca04ddcaa9d07adbba43c91
Source dataset
uspto-grants-1997_04
Patent number
US05623074

Reaction notes

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