Sulfuric Acid → 7,8-Dimethoxy-4-(3,4-dimethoxyphenyl)-1,2,3,4-tetrahydroisoquinoline

HRID 486372노트

반응식

HRID 486372 반응식
[CH3:1][O:2][C:3]1[C:23]([O:24][CH3:25])=[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>FC(F)(F)C(O)=O>[CH3:25][O:24][C:23]1[C:3]([O:2][CH3:1])=[C:4]2[C:20]([CH:8]([C:9]3[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([O:17][CH3:18])[CH:10]=3)[CH2:7][NH:6][CH2:5]2)=[CH:21][CH:22]=1

참가 물질

4

반응물 2

HCID 1118Sulfuric AcidHCID 14719553alpha-[[(2,3-Dimethoxybenzyl)amino]methyl]-3,4-dimethoxybenzyl alcohol

생성물 1

HCID 147195577,8-Dimethoxy-4-(3,4-dimethoxyphenyl)-1,2,3,4-tetrahydroisoquinoline수율 84%

시약·촉매·용매 1

HCID 6422Trifluoroacetic acid용매

실험 절차

α-[[(2,3-Dimethoxybenzyl)amino]methyl]-3,4-dimethoxybenzyl alcohol 6.56 g, 18.9 mmol) was dissolved in trifluoroacetic acid (50 ml). Concentrated sulfuric acid was added to the solution under stirring and under cooling with ice and the reaction was conducted under these conditions for 40 minutes. The reaction solution was concentrated. Water was added to the residue and then it was made basic with aqueous ammonia under stirring and under cooling with ice. After extraction with dichloromethane, the dichloromethane layer was washed with a saturated sodium chloride aqueous solution and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the resultant crystals were washed with isopropyl ether to obtain 5.23 g of 7,8-dimethoxy-4-(3,4-dimethoxyphenyl)-1,2,3,4-tetrahydroisoquinoline.

후처리

  1. temperatureunder cooling with ice
  2. concentrationThe reaction solution was concentrated
  3. additionWater was added to the residue
  4. stirringunder stirring
  5. temperatureunder cooling with ice
  6. extractionAfter extraction with dichloromethane
  7. washthe dichloromethane layer was washed with a saturated sodium chloride aqueous solution
  8. dry with materialdried over anhydrous magnesium sulfate
  9. distillationThe solvent was distilled off under reduced pressure
  10. washthe resultant crystals were washed with isopropyl ether

출처 및 근거

ORD 기록
ord-ce673e785c57416fbcae6b3b94c4ca69
출처 데이터셋
uspto-grants-1994_03
특허 번호
US05292521

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