4-(Trifluoromethoxy)phenylhydrazine hydrochloride → 2-methyl-8-trifluoromethoxy-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole

HRID 1400333Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1400333
Cl.[F:2][C:3]([F:14])([F:13])[O:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11]N)=[CH:7][CH:6]=1.Cl.[CH3:16][N:17]1[CH2:22][CH2:21][C:20](=O)[CH2:19][CH2:18]1>S(=O)(=O)(O)O.O1CCOCC1>[CH3:16][N:17]1[CH2:22][CH2:21][C:20]2[NH:11][C:8]3[CH:7]=[CH:6][C:5]([O:4][C:3]([F:14])([F:13])[F:2])=[CH:10][C:9]=3[C:19]=2[CH2:18]1

Komponenten

5

Edukt 2

HCID 27773284-(Trifluoromethoxy)phenylhydrazine hydrochlorideHCID 122100571-Methylpiperidin-4-one hydrochloride

Produkt 1

HCID 594549332-methyl-8-trifluoromethoxy-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1118Sulfuric AcidLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

(4-(Trifluoromethoxy)phenyl)hydrazine hydrochloride (1 equiv.) is taken in 7% sulfuric acid in 1,4-dioxane. 1-Methylpiperidin-4-one hydrochloride (0.76-1.4 equiv.) is added and the mixture is stirred at 80° C. for 6 h. The reaction is monitored by TLC and LCMS. After completion of the reaction, the reaction mixture is concentrated, then slowly quenched with aq. NaHCO3 solution and extracted with EtOAc. The organic layer is dried over anhydrous sodium sulfate, evaporated to dryness and purified by column chromatography to afford 2-methyl-8-(trifluoromethoxy)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole.

Aufarbeitung

  1. customAfter completion of the reaction
  2. concentrationthe reaction mixture is concentrated
  3. customslowly quenched with aq. NaHCO3 solution
  4. extractionextracted with EtOAc
  5. dry with materialThe organic layer is dried over anhydrous sodium sulfate
  6. customevaporated to dryness
  7. custompurified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-fb4e43e11b384b9a841c6f9aa906b4b2
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08906925B2

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