Acrylonitrile → 3-{[(1-Benzylpiperidin-4-yl)methyl]amino}propanenitrile

HRID 367278Notes

Reaction equation

HRID 367278 reaction equation
[C:1]1([CH2:7][N:8]2[CH2:13][CH2:12][CH:11]([CH2:14][NH2:15])[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:16](#[N:19])[CH:17]=[CH2:18]>C(O)C>[C:1]1([CH2:7][N:8]2[CH2:13][CH2:12][CH:11]([CH2:14][NH:15][CH2:18][CH2:17][C:16]#[N:19])[CH2:10][CH2:9]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 7855AcrylonitrileHCID 1514444(1-Benzyl-4-piperidyl)methanamine

Product 1

HCID 225732293-{[(1-Benzylpiperidin-4-yl)methyl]amino}propanenitrileYield 102.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-(phenylmethyl)-4-piperidinemethanamine (0.076 mol) and acrylonitrile (0.076 mol) in ethanol (250 ml) was stirred and refluxed for 4 hours. The solvent was evaporated, yielding 20.0 g (102.4%, crude residue, used in next reaction step, without further purification) of 3-[[[1-(phenylmethyl)-4-piperidinyl]methyl]amino]-propanenitrile (interm. 14).

Workup

  1. temperaturerefluxed for 4 hours
  2. customThe solvent was evaporated

Sources & evidence

ORD record
ord-91e6ed665a5d4a989f783b427a6ffcba
Source dataset
uspto-grants-2000_10
Patent number
US06133277

Reaction notes

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