Sulfuric Acid → HCID 10802931, compound

HRID 2352250Notes

Reaction equation

HRID 2352250 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:20]=[CH:21][CH:22]=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>FC(F)(F)C(O)=O>[CH3:18][O:17][C:11]1[CH:10]=[C:9]([CH:8]2[C:20]3[C:4](=[CH:3][C:2]([CH3:1])=[CH:22][CH:21]=3)[CH2:5][NH:6][CH2:7]2)[CH:14]=[CH:13][C:12]=1[O:15][CH3:16]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 10709437HCID 10709437, compound

Product 1

HCID 10802931HCID 10802931, compoundYield 51.4%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

1.8 g of α-[[(3-methylbenzyl)amino]methyl]-3,4-dimethoxybenzyl alcohol was dissolved in 13.5 ml of trifluoroacetic acid, and after adding thereto 0.41 ml of conc, sulfuric acid under ice cooling, the mixture was allowed to react for 40 minutes. The reaction solution was concentrated, and subjected to azeotropic distillation with chloroform 2 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 once, and dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was subjected to silica gel column chromatography (chloroform-methanol-28% aqueous ammonia (15:1:0.1); a material of Rf being 0.46 [Kiesel gel 60F254 plate, chloroform-methanol-28% aqueous ammonia (15:1:0.1)]was collected, recrystallized from chloroform-n-hexane, and recrystallized from the same solvent system several times, giving 870 mg of 4-(3,4-dimethoxyphenyl)-7-methyl-1,2,3,4-tetrahydroisoquinoline, m.p. 129°-131° C.

Workup

  1. additionafter adding
  2. customto react for 40 minutes
  3. concentrationThe reaction solution was concentrated
  4. distillationsubjected to azeotropic distillation with chloroform 2 times
  5. additionafter adding chloroform
  6. additionthe mixture was basified by addition of 28% aqueous ammonia
  7. customBy a separating procedure, the chloroform layer was collected
  8. washwashed with water once
  9. dry with materialdried over anhydrous sodium sulfate
  10. distillationThe solvent was distilled off
  11. customcollected
  12. customrecrystallized from chloroform-n-hexane
  13. customrecrystallized from the same solvent system several times

Sources & evidence

ORD record
ord-fba1064817594f99adce7ae00fea7cfb
Source dataset
uspto-grants-1989_10
Patent number
US04876261

Reaction notes

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