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

HRID 1294468Notes

Reaction equation

HRID 1294468 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][CH:10]([CH2:14][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 178701734-(1-Benzylpiperidin-3-yl)butylamine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

8.0 g (33.3 mmol) 4-(1-benzylpiperidin-3-yliden)-butyronitrile are dissolved in 80 ml ethanol and added to a spatula tip of Raney-Nickel. The mixture is stirred at ca. 50° C. under hydrogen atmosphere until consumption of the theoretischen amount of hydrogen to be taken up (ca. 5 days). The mixture is filtrated from the catalyst and the solvent is removed under vacuum. The residue is chromatographically purified twice 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 filtrated from the catalyst
  3. customthe solvent is removed under vacuum
  4. customThe residue is chromatographically purified twice over silica gel with CHCl3/CH3OH/NH4OH (90/10/1)
  5. customa colorless oil remains which is further processed without additional purification

Sources & evidence

ORD record
ord-6b99c749f37d4e3282dc28a7636bcdf6
Source dataset
uspto-grants-2007_07
Patent number
US07241745B2

Reaction notes

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