Hydrochloric Acid → 4-(2-(3,4-Dihydro-6,7-dimethoxy-2(1H)-isoquinolinyl)ethyl)benzenamine

HRID 1192844노트

반응식

HRID 1192844 반응식
Cl.C(O)C.[CH3:5][O:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][C:16]=1[O:17][CH3:18])[CH2:13][N:12]([CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([N+:27]([O-])=O)=[CH:23][CH:22]=1)[CH2:11][CH2:10]2.[OH-].[Na+]>[Fe].O.ClCCl.C(Cl)(Cl)Cl.CO>[CH3:5][O:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][C:16]=1[O:17][CH3:18])[CH2:13][N:12]([CH2:19][CH2:20][C:21]1[CH:22]=[CH:23][C:24]([NH2:27])=[CH:25][CH:26]=1)[CH2:11][CH2:10]2

참가 물질

9

반응물 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 104274766,7-Dimethoxy-2-[2-(4-nitrophenyl)ethyl]-1,2,3,4-tetrahydroisoquinoline

생성물 1

HCID 100412274-(2-(3,4-Dihydro-6,7-dimethoxy-2(1H)-isoquinolinyl)ethyl)benzenamine수율 90%

시약·촉매·용매 4

HCID 23925Iron촉매HCID 962Water용매HCID 6344Dichloromethane용매HCID 21584188Chloroform methanol용매

반응 조건

온도
80 °C

실험 절차

Iron (1.27 kg, 23.48 mol), hydrochloric acid (127 mL, 1.54 mol) and 6.7 L of 50% aqueous ethanol were added to a reactor, and stirred for 1 hour at 80° C. 6,7-dimethoxy-2-(4-nitrophenethyl)-1,2,3,4-tetrahydroisoquinoline (1.3 kg, 3.91 mol) obtained in Step 1-1 was slowly added thereto for one hour, followed by stirring for 3 hours at 80° C. After checking completion of the reaction by thin layer chromatography (eluent: chloroform/methanol=15/1), the reaction mixture was cooled to room temperature. 5.3 L of dichloromethane and 5.3 L of water were added thereto, the reaction mixture was neutralized by adding 804 mL of 10% aqueous sodium hydroxide. The resulting mixture was filtered through a Celite pad and washed with 3 L of methylenechloride. The organic layer was collected, dried over magnesium sulfate, and then filtered. The solvent was removed under reduced pressure, and dried with hot air at 40° C. in an oven to obtain the title compound (1.05 kg, 90%).

후처리

  1. waitfor one hour
  2. stirringby stirring for 3 hours at 80° C
  3. temperaturethe reaction mixture was cooled to room temperature
  4. filtrationThe resulting mixture was filtered through a Celite pad
  5. washwashed with 3 L of methylenechloride
  6. customThe organic layer was collected
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customThe solvent was removed under reduced pressure
  10. customdried with hot air at 40° C. in an oven

출처 및 근거

ORD 기록
ord-c91960c4ba274f3996983cec5ccbe8db
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08680277B2

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