Sulfuric Acid → 6-((E)-2-(4-fluorophenyl)prop-1-enyl)-1,2,3,4,5,6-hexahydro-3,9-dimethylazepino[4,5-b]indole
Reaktionsgleichung
[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]=1Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 90 °C
Versuchsvorschrift
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.
Aufarbeitung
- temperatureThe reaction mixture was cooled
- extractionextracted with ethyl acetate
- dry with materialThe organic layer was dried over anhydrous sodium sulfate
- customevaporated under reduced pressure
- customThe crude product was purified
Quellen und Nachweise
- ORD-Eintrag
- ord-e2dce95dcea647328535da7c35d7cd59
- Quelldatensatz
- uspto-grants-2013_10
- Patentnummer
- US08569287B2
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