Acrylonitrile → HCID 21999706, compound

HRID 1871256Notes

Reaction equation

HRID 1871256 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].[C:15](#[N:18])[CH:16]=[CH2:17]>[Cl-].C[N+](CCCCCCCC)(CCCCCCCC)CCCCCCCC.CC(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:14][CH2:13][N:12]([CH2:17][CH2:16][C:15]#[N:18])[CH2:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 2

HCID 7855AcrylonitrileHCID 936011-(3,4-Dichlorophenyl)piperazine

Product 1

HCID 21999706HCID 21999706, compoundYield 98.5%

Reagents, catalysts & solvents 2

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 3776IsopropanolSolvent

Procedure

A mixture of 1-(3,4-dichlorophenyl)piperazine (0.1 mol), 2-propenenitrile (0.15 mol), and N-methyl-N,N-dioctyl octanaminiumchloride (1 ml) in 2-propanol (150 ml) was stirred and refluxed for one hour. The solvent was evaporated and the residue was purified by column chromatography over silica gel (eluent: CH2Cl2 /CH3OH 95/5). The pure fractions were collected and the solvent was evaporated. The residue was stirred in diisopropylether/acetonitrile 10/1. The solvent was evaporated, yielding 28 g (98.5%) of 4-(3,4-dichlorophenyl)-1-piperazinepropanenitrile (interm. 3).

Workup

  1. temperaturerefluxed for one hour
  2. customThe solvent was evaporated
  3. customthe residue was purified by column chromatography over silica gel (eluent: CH2Cl2 /CH3OH 95/5)
  4. customThe pure fractions were collected
  5. customthe solvent was evaporated
  6. stirringThe residue was stirred in diisopropylether/acetonitrile 10/1
  7. customThe solvent was evaporated

Sources & evidence

ORD record
ord-af43fd9d90ab4adba2fd941d272a38f3
Source dataset
uspto-grants-2000_08
Patent number
US06103725

Reaction notes

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