Acrylonitrile → 4-(2,6-Dimethylphenyl)-1-piperazinepropanenitrile

HRID 1070701Notes

Reaction equation

HRID 1070701 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[N:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1.[C:15](#[N:18])[CH:16]=[CH2:17]>CO>[CH3:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[C:3]=1[N:9]1[CH2:10][CH2:11][N:12]([CH2:17][CH2:16][C:15]#[N:18])[CH2:13][CH2:14]1

Participants

4

Reactant 2

HCID 7855AcrylonitrileHCID 705381-(2,6-Xylyl)piperazine

Product 1

HCID 223975344-(2,6-Dimethylphenyl)-1-piperazinepropanenitrileYield 78.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-(2,6-Dimethylphenyl) piperazine (1 g, 5.23 mmol) in MeOH (10 ml) was cooled to 0° and 0.305 g (5.73 mmol) of acrilonitrile was added. The reaction was stirred overnight at room temperature and evaporated under vacuum affording 1 g of crude 3-[4-(2,6-dimethylphenyl)piperazin-1-yl]propionitrile as a waxy solid. This compound was dissolved in MeOH (60 ml), 2 ml 37% HCl and hydrogenated under pressure (40 psi) with 0.2 g of 10% Pd\C. The reaction was filtered and evaporated to dryness obtaining 1 g of the title compound, as a hydrochloride salt, that was used without further purification for the following reaction.

Workup

  1. customevaporated under vacuum

Sources & evidence

ORD record
ord-b9433cbfcbeb47489e0922af4d1aaeaa
Source dataset
uspto-grants-2005_06
Patent number
US06903117B2

Reaction notes

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