Sulfuric Acid → 4-(3,4-Dimethoxyphenyl)-8-methyl-1,2,3,4-tetrahydroisoquinoline
Reaction equation
CO[C:3]1[CH:23]=[CH:22][CH:21]=[CH:20][C:4]=1[CH2:5][NH:6][CH2:7][CH:8](O)[C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([O:17][CH3:18])[CH:10]=1.S(=O)(=O)(O)O.F[C:30](F)(F)C(O)=O>>[CH3:18][O:17][C:11]1[CH:10]=[C:9]([CH:8]2[C:3]3[C:4](=[C:20]([CH3:30])[CH:21]=[CH:22][CH:23]=3)[CH2:5][NH:6][CH2:7]2)[CH:14]=[CH:13][C:12]=1[O:15][CH3:16]Participants
Procedure
900 mg of α-[[(2-methoxybenzylamino]methyl]-3,4-dimethoxybenzyl alcohol was dissolved in 7 ml of trifluoroacetic acid, and after adding thereto 0.21 ml of conc. sulfuric acid under ice cooling, the mixture was allowed to react for 60 minutes. The reaction solution was concentrated, and subjected to azeotropic distillation 3 times, and after adding chloroform, the mixture was basified by addition of 28% aqueous ammonia. By a separating procedure, the chloroform layer was collected, washed with water, and dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue obtained was recrystallized from ethyl acetate-n-hexane, giving 440 mg of 4-(3,4-dimethoxyphenyl)-8-methyl-1,2,3,4-tetrahydroisoquinoline, m.p. 86°-88° C.
Workup
- additionafter adding
- customto react for 60 minutes
- concentrationThe reaction solution was concentrated
- distillationsubjected to azeotropic distillation 3 times
- additionafter adding chloroform
- additionthe mixture was basified by addition of 28% aqueous ammonia
- customBy a separating procedure, the chloroform layer was collected
- washwashed with water
- dry with materialdried over anhydrous sodium sulfate
- distillationThe solvent was distilled off
- customthe residue obtained
- customwas recrystallized from ethyl acetate-n-hexane
Sources & evidence
- ORD record
- ord-4e5191db20264d89a341c95b5ddf77bb
- Source dataset
- uspto-grants-1993_04
- Patent number
- US05204468
Reaction notes
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