Piperonylamine → 8-methyl-5-(2-(6-(trifluoromethyl)pyridin-3-yl)ethyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole

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Reaktionsgleichung

[C:1]1([CH3:21])[CH:6]=[CH:5][C:4]([N:7]([CH2:9][CH2:10][C:11]2[CH:12]=[CH:13][C:14]([C:17]([F:20])([F:19])[F:18])=[N:15][CH:16]=2)N)=[CH:3][CH:2]=1.Cl.O.[NH:24]1[CH2:29][CH2:28][C:27](=O)[CH2:26][CH2:25]1>O1CCOCC1.C(O)(C(F)(F)F)=O.C([O-])(O)=O.[Na+]>[CH3:21][C:1]1[CH:6]=[CH:5][C:4]2[N:7]([CH2:9][CH2:10][C:11]3[CH:16]=[N:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=3)[C:27]3[CH2:28][CH2:29][NH:24][CH2:25][C:26]=3[C:3]=2[CH:2]=1

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

5-(2-(1-p-Tolylhydrazinyl)ethyl)-2-(trifluoromethyl)pyridine (88 mg, 0.29 mmol) was dissolved in 1,4-dioxane (2 mL) and 4-piperidone hydrate hydrochloride was added with one drop of TFA. The reaction mixture became acidic. The mixture was heated at 100° C. for 2 h. The reaction was monitored by TLC and LCMS. After completion of reaction, the mixture was diluted with sat. NaHCO3 solution and extracted with EtOAc. The organic extracts were dried over anhydrous sodium sulfate and concentrated. The compound was purified by reverse phase chromatography. 1HNMR (CD3OD, TFA salt) d (ppm): 8.20 (s, 1H), 7.60 (m, 2H), 7.25 (d, 1H), 7.18 (d, 1H), 6.98 (d, 1H), 4.40 (m, 4H), 3.50 (t, 2H), 3.20 (m, 2H), 2.82 (t, 2H), 2.40 (s, 3H).

Aufarbeitung

customAfter completion of reaction
extractionextracted with EtOAc
dry with materialThe organic extracts were dried over anhydrous sodium sulfate
concentrationconcentrated
customThe compound was purified by reverse phase chromatography

Quellen und Nachweise

ORD-Eintrag: ord-7b2280d4ac3642bb92b9cec848984728
Quelldatensatz: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09255094B2

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