4-(1-Benzylpiperidin-3-yliden)-butyronitrile → 4-(1-Benzylpiperidin-3-ylidene)-butylamine

HRID 1280787Notes

Reaction equation

HRID 1280787 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH2:11][C:10](=[CH:14][CH2:15][CH2:16][C:17]#[N:18])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H]>C(O)C.[Ni]>[CH2:1]([N:8]1[CH2:13][CH2:12][CH2:11][C:10](=[CH:14][CH2:15][CH2:16][CH2:17][NH2:18])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 539871944-(1-Benzylpiperidin-3-yliden)-butyronitrileHCID 178418361HCID 178418361, compound

Product 1

HCID 701595444-(1-Benzylpiperidin-3-ylidene)-butylamine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

8.0 g (33.3 mmol) 4-(1-benzylpiperidin-3-ylidene)-butyronitrile are dissolved in 80 ml ethanol and added to a spatula tip of Raney-Nickel. The mixture is stirred under hydrogen atmosphere until consumption of the theoretical amount of hydrogen to be taken up (ca. 5 days). The mixture is filtered from the catalyst and the solvent is removed under vacuum. The residue is chromatographically purified Voice over silica gel with CHCl3/CH3OH/NH4OH (90/10/1). After drawing off the solvent, a colorless oil remains which is further processed without additional purification. Yield. 3.9 g (47%)

Workup

  1. custom(ca. 5 days)
  2. filtrationThe mixture is filtered from the catalyst
  3. customthe solvent is removed under vacuum
  4. customa colorless oil remains which is further processed without additional purification
  5. customYield

Sources & evidence

ORD record
ord-7c05bd4657534792bcff8dc8480c28f0
Source dataset
uspto-grants-2002_09
Patent number
US06451816B1

Reaction notes

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