3-Piperidinone, 1-(phenylmethyl)- → 4-(1-Benzylpiperidin-3-yliden)-butyronitrile

HRID 1280786

Reaktionsgleichung

Reaktionsgleichung von HRID 1280786
[Br-].[C:2]([CH2:4][CH2:5][CH2:6][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)#[N:3].[CH2:26]([N:33]1[CH2:38][CH2:37][CH2:36][C:35](=O)[CH2:34]1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>>[CH2:26]([N:33]1[CH2:38][CH2:37][CH2:36][C:35](=[CH:6][CH2:5][CH2:4][C:2]#[N:3])[CH2:34]1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Komponenten

3

Edukt 2

HCID 966503-Piperidinone, 1-(phenylmethyl)-HCID 3036619(3-Cyanopropyl)triphenylphosphonium bromide

Produkt 1

HCID 539871944-(1-Benzylpiperidin-3-yliden)-butyronitrile

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

77.3 g (188.3 mmol) 3-cyanopropyl triphenylphosphonium bromide are suspended in 300 ml tolueneand added to 22.0 g (191.9 mmol) potassium-tert-butylate. The mixture is cooled to ca. 0° C. under moisture exclusion and a solution of 34.6 g (182.8 mmol) 1-benzyl-3-piperidone in 50 ml tolueneare added dropwise under cooling. The batch is left to stand overnight at ca. 0° C., subsequently diluted with 200 ml tolueneand washed twice, each with 100 ml water. The organic phase is extracted with 150 ml half-concentrated hydrochloric acid. Subsequently, the aqueous phase is made basic with 200 ml 10% sodium hydroxide solution and extracted twice, each with 250 ml toluol. The solvent is removed under vacuum and the residue is chromatographically purified over silica gel with CHCl3/CH3OH (97/3). After drawing off the solvent, a light brown oil remains which is further processed without additional purification. Yield: 47.4 g (90%).

Aufarbeitung

  1. temperatureunder cooling
  2. waitThe batch is left
  3. additionsubsequently diluted with 200 ml
  4. washwashed twice
  5. extractionThe organic phase is extracted with 150 ml half-concentrated hydrochloric acid
  6. extractionextracted twice
  7. customThe solvent is removed under vacuum
  8. customthe residue is chromatographically purified over silica gel with CHCl3/CH3OH (97/3)
  9. customa light brown oil remains which is further processed without additional purification

Quellen und Nachweise

ORD-Eintrag
ord-948cf75ec249484cb1ee716fd62869d7
Quelldatensatz
uspto-grants-2002_09
Patentnummer
US06451816B1

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