(E)-3-(1-benzylpiperidin-4-yl)-2-propenenitrile → 3-(1-Benzylpiperidin-4-yl)propanenitrile

HRID 54553Notes

Reaction equation

HRID 54553 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11](/[CH:14]=[CH:15]/[C:16]#[N:17])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CO.[Pt](=O)=O>[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

Participants

4

Reactant 1

HCID 19959219(E)-3-(1-benzylpiperidin-4-yl)-2-propenenitrile

Product 1

HCID 199592563-(1-Benzylpiperidin-4-yl)propanenitrileYield 48.7%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

A mixture of (E)-3-(1-benzylpiperidin-4-yl)-2-propenenitrile (5.5 g) and platinum(IV) oxide (0.5 g) in methanol (70 ml) was hydrogenated at atmospheric pressure for 8 hours. After platinum(IV) oxide was removed by filtration, the filtrate was evaporated in vacuo to give 3-(1-benzylpiperidin-4-yl)propanenitrile (2.7 g) as an oil.

Workup

  1. customAfter platinum(IV) oxide was removed by filtration
  2. customthe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-fbff4cd895f240f5b72f30be0cb0df21
Source dataset
uspto-grants-1997_04
Patent number
US05622976

Reaction notes

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