Sulfuric Acid → 6-((E)-2-(4-fluorophenyl)prop-1-enyl)-1,2,3,4,5,6-hexahydro-3,9-dimethylazepino[4,5-b]indole

HRID 1481423노트

반응식

HRID 1481423 반응식
[CH3:1][N:2]1[CH2:15][CH2:14][C:13]2[C:12]3[CH:11]=[C:10]([CH3:16])[CH:9]=[CH:8][C:7]=3[N:6]([CH2:17][C:18]([C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=3)(O)[CH3:19])[C:5]=2[CH2:4][CH2:3]1.OS(O)(=O)=O.[OH-].[K+]>O>[F:27][C:24]1[CH:23]=[CH:22][C:21](/[C:18](/[CH3:19])=[CH:17]/[N:6]2[C:7]3[CH:8]=[CH:9][C:10]([CH3:16])=[CH:11][C:12]=3[C:13]3[CH2:14][CH2:15][N:2]([CH3:1])[CH2:3][CH2:4][C:5]2=3)=[CH:26][CH:25]=1

참가 물질

5

반응물 3

HCID 1118Sulfuric AcidHCID 14797Potassium HydroxideHCID 593683271-(3,9-Dimethyl-2,3,4,5-tetrahydroazepino[4,5-b]indol-6(1H)-yl)-2-(4-fluorophenyl) propan-2-ol

생성물 1

HCID 593681396-((E)-2-(4-fluorophenyl)prop-1-enyl)-1,2,3,4,5,6-hexahydro-3,9-dimethylazepino[4,5-b]indole

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
90 °C

실험 절차

The title compound was prepared by following general procedure 6. 1-(3,9-Dimethyl-2,3,4,5-tetrahydroazepino[4,5-b]indol-6(1H)-yl)-2-(4-fluorophenyl)propan-2-ol (100 mg, 0.273 mmol) was taken into 2.0 mL of 25% H2SO4 in water, and stirred at 90° C. for 2 h. The reaction was monitored by TLC and LCMS. The reaction mixture was cooled and basified with aq. KOH solution and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and evaporated under reduced pressure. The crude product was purified using reverse phase chromatography to afford 10 mg of product as the TFA salt along with 6-(2-(4-fluorophenyl)allyl)-3,9-dimethyl-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole.

후처리

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. customevaporated under reduced pressure
  5. customThe crude product was purified

출처 및 근거

ORD 기록
ord-d0c201fe22824511a947cb19cfe49540
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09409910B2

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