Ammonium Hydroxide → 3-(1-Benzylpiperidin-4-yl)propan-1-amine

HRID 54554Notes

Reaction equation

HRID 54554 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][C:16]#[N:17])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH4+].[OH-]>[Ni].C(O)C>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][CH2:16][NH2:17])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 14923Ammonium HydroxideHCID 199592563-(1-Benzylpiperidin-4-yl)propanenitrile

Product 1

HCID 199592053-(1-Benzylpiperidin-4-yl)propan-1-amineYield 78.6%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A mixture of 3-(1-benzylpiperidin-4-yl)propanenitrile (0.5 g), Raney nickel (0.3 ml) and a conc. ammonia aqueous solution (1 ml) in ethanol (10 ml) was hydrogenated at atmospheric pressure for 6 hours. After Raney nickel was removed by filtration, the filtrate was evaporated in vacuo. The residue was chromatographed on alumina eluting with 2% methanol in chloroform and the fractions containing the object product were collected and evaporated to give 3-(1-benzylpiperidin-4-yl)propylamine (0.4 g) as an oil.

Workup

  1. customAfter Raney nickel was removed by filtration
  2. customthe filtrate was evaporated in vacuo
  3. customThe residue was chromatographed on alumina eluting with 2% methanol in chloroform
  4. additionthe fractions containing the object product
  5. customwere collected
  6. customevaporated

Sources & evidence

ORD record
ord-b684a9927b4f4434827faf834b653fd7
Source dataset
uspto-grants-1997_04
Patent number
US05622976

Reaction notes

Loading…