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

HRID 1294467

Reaction equation

HRID 1294467 reaction equation
[Br-].[C:2]([CH2:4][CH2:5][CH2:6][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)#[N:3].CC([O-])(C)C.[K+].[CH2:32]([N:39]1[CH2:44][CH2:43][CH2:42][C:41](=O)[CH2:40]1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>C1(C)C=CC=CC=1>[CH2:32]([N:39]1[CH2:44][CH2:43][CH2:42][C:41](=[CH:6][CH2:5][CH2:4][C:2]#[N:3])[CH2:40]1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

5

Reactant 3

HCID 966503-Piperidinone, 1-(phenylmethyl)-HCID 3036619(3-Cyanopropyl)triphenylphosphonium bromideHCID 23665647Potassium tert-butoxide

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent3×

Procedure

77.3 g (188.3 mmol) 3-cyanopropyl-triphenylphosphonium bromide are suspended in 300 ml toluene and 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 toluene is added dropwise under cooling. The batch is left to stand overnight at ca. 0° C. and subsequently diluted with 200 ml toluene and 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 toluene.

Workup

  1. temperatureThe mixture is cooled to ca 0° C. under moisture exclusion
  2. temperatureunder cooling
  3. waitThe batch is left
  4. washwashed twice
  5. extractionThe organic phase is extracted with 150 ml half concentrated hydrochloric acid
  6. extractionextracted twice

Sources & evidence

ORD record
ord-3f7745a5be8c402ab5eab096d3914222
Source dataset
uspto-grants-2007_07
Patent number
US07241745B2

Linked notes

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