Trifluoroacetic acid → 5-allyl-4-[2-(4-fluoro-phenyl)-allyl]-2,4,8-trimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole

HRID 576514

Reaktionsgleichung

[CH2:1]([N:4]([C:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][CH:7]=1)N)[CH:2]=[CH2:3].[F:13][C:14]1[CH:19]=[CH:18][C:17]([C:20](=[CH2:31])[CH2:21][C:22]2([CH3:30])[C:27](=O)[CH2:26][CH2:25][N:24]([CH3:29])[CH2:23]2)=[CH:16][CH:15]=1.FC(F)(F)C(O)=O>O1CCOCC1>[CH2:1]([N:4]1[C:6]2[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][C:7]=2[C:26]2[CH2:25][N:24]([CH3:29])[CH2:23][C:22]([CH2:21][C:20]([C:17]3[CH:16]=[CH:15][C:14]([F:13])=[CH:19][CH:18]=3)=[CH2:31])([CH3:30])[C:27]1=2)[CH:2]=[CH2:3]

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

N-Allyl-N-p-tolyl-hydrazine (600 mg, 3.70 mmol) and 3-[2-(4-fluoro-phenyl)-allyl]-1,3-dimethyl-piperidin-4-one (970 mg, 3.71 mmol) were dissolved in 1,4-dioxane (4 mL). Trifluoroacetic acid (1 mL) was added and the reaction mixture was heated to 100° C. for 3 h. 1,4-Dioxane was removed under reduced pressure, the residue was basified with aqueous sodium bicarbonate, and extracted with EtOAc (2×30 mL). The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography over silica gel (100-200 mesh, eluent as 5% EtOAc in hexane) to obtain 290 mg of 5-allyl-4-[2-(4-fluoro-phenyl)-allyl]-2,4,8-trimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole.

Aufarbeitung

custom1,4-Dioxane was removed under reduced pressure
extractionextracted with EtOAc (2×30 mL)
dry with materialThe organic layer was dried over sodium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by column chromatography over silica gel (100-200 mesh, eluent as 5% EtOAc in hexane)

Quellen und Nachweise

ORD-Eintrag: ord-a19e3a35ee5c4015bc2ae9aebf57ee06
Quelldatensatz: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09040519B2

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