Carbazole → 1-(3-Carbazolyl)-3-(1-acetylpiperidin-4-yl)-1-propanone

HRID 2293444

Reaktionsgleichung

[CH:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[C:14]([N:17]1[CH2:22][CH2:21][CH:20]([CH2:23][CH2:24][C:25](Cl)=[O:26])[CH2:19][CH2:18]1)(=[O:16])[CH3:15].[Cl-].[Al+3].[Cl-].[Cl-]>[N+](C)([O-])=O>[CH:10]1[C:11]2[NH:12][C:13]3[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=3)[C:6]=2[CH:7]=[C:8]([C:25](=[O:26])[CH2:24][CH2:23][CH:20]2[CH2:21][CH2:22][N:17]([C:14](=[O:16])[CH3:15])[CH2:18][CH2:19]2)[CH:9]=1

Komponenten

Reaktionsbedingungen

Temperatur: 70 °C

Versuchsvorschrift

To a 90 ml solution of 5.0 g of carbazole and 7.2 g of 3-(1-acetylpiperidin-4-yl)propionyl chloride in nitromethane, 9.3 g of aluminum chloride was added little by little, followed by stirring at 70° C. for 11 hours. The reaction mixture was poured over 100 ml of ice water, and the organic layer was separated and then washed by sequential additions of a 50 ml saturated aqueous sodium hydrogen carbonate solution and 50 ml of distilled water. After the mixture was dried over anhydrous sodium sulfate, the solvent was distilled off to yield an oily residue. The residue was purified by silica gel column chromatography (developing solvent: ethyl acetate-methanol=20:1 (v/v)) to yield 2.6 g of the title compound as a light yellow powder.

Aufarbeitung

customthe organic layer was separated
washwashed by sequential additions of a 50 ml saturated aqueous sodium hydrogen carbonate solution and 50 ml of distilled water
dry with materialAfter the mixture was dried over anhydrous sodium sulfate
distillationthe solvent was distilled off
customto yield an oily residue
customThe residue was purified by silica gel column chromatography (developing solvent: ethyl acetate-methanol=20:1 (v/v))

Quellen und Nachweise

ORD-Eintrag: ord-b07666e1600a4b04a5ebba839dbd1e33
Quelldatensatz: uspto-grants-1997_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05686466

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