Acetaldehyde → 1-Cyano-1-(4-diethylaminophenyl)cyclopentane

HRID 2050899

Reaktionsgleichung

Reaktionsgleichung von HRID 2050899
[C:1]([C:3]1([C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][CH:9]=2)[CH2:7][CH2:6][CH2:5][CH2:4]1)#[N:2].[H][H].[CH:19](=O)[CH3:20].[CH2:22](O)[CH3:23]>[Pd]>[C:1]([C:3]1([C:8]2[CH:13]=[CH:12][C:11]([N:14]([CH2:19][CH3:20])[CH2:22][CH3:23])=[CH:10][CH:9]=2)[CH2:7][CH2:6][CH2:5][CH2:4]1)#[N:2]

Komponenten

6

Edukt 4

HCID 177AcetaldehydeHCID 702EthanolHCID 43519051-(4-Nitrophenyl)cyclopentane-1-carbonitrileHCID 178418361HCID 178418361, Verbindung3×

Produkt 1

HCID 198341171-Cyano-1-(4-diethylaminophenyl)cyclopentane

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 23938PalladiumKatalysator2×

Versuchsvorschrift

In a pressure reactor was placed 43.4 g (0.2 mole) of 1-cyano-1-(4-nitrophenyl)cyclopentane and 500 mL of absolute ethanol. One gram of 5% Pd/C was added, the reactor charged with hydrogen and shaken at room temperature until the theoretical amount of hydrogen had been taken up. The reactor was vented and 22 g (0.5 mole) of acetaldehyde and 2 g of 10% Pd/C was added. The reactor was charged with hydrogen and shaken at room temperature for 16 hours. The reaction mixture was then filtered and the filtrate concentrated in vacuo. The product was purified by chromatography, using a gradient of 90% hexane: 10% ethylacetate to 70% hexane: 30% ethylacetate as eluant. There was obtained 10.7 g of a clear oil.

Aufarbeitung

  1. customIn a pressure reactor was placed
  2. filtrationThe reaction mixture was then filtered
  3. concentrationthe filtrate concentrated in vacuo
  4. customThe product was purified by chromatography

Quellen und Nachweise

ORD-Eintrag
ord-0ad487086dea4a00aeb59f61f85a9439
Quelldatensatz
uspto-grants-1991_05
Patentnummer
US05015644

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