Sulfuric Acid → 4-(3,4-Dimethoxyphenyl)-8-methyl-1,2,3,4-tetrahydroisoquinoline

HRID 1590827노트

반응식

HRID 1590827 반응식
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]

참가 물질

4

반응물 3

HCID 1118Sulfuric AcidHCID 6422Trifluoroacetic acidHCID 20531701HCID 20531701, 화합물

생성물 1

HCID 105170974-(3,4-Dimethoxyphenyl)-8-methyl-1,2,3,4-tetrahydroisoquinoline

실험 절차

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.

후처리

  1. additionafter adding
  2. customto react for 60 minutes
  3. concentrationThe reaction solution was concentrated
  4. distillationsubjected to azeotropic distillation 3 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
  9. dry with materialdried over anhydrous sodium sulfate
  10. distillationThe solvent was distilled off
  11. customthe residue obtained
  12. customwas recrystallized from ethyl acetate-n-hexane

출처 및 근거

ORD 기록
ord-4e5191db20264d89a341c95b5ddf77bb
출처 데이터셋
uspto-grants-1993_04
특허 번호
US05204468

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