Sodium Carbonate → 4-(3,4-Dichlorophenyl)-1-piperazinepentanenitrile

HRID 1975878

Reaktionsgleichung

Reaktionsgleichung von HRID 1975878
[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].Cl[CH2:16][CH2:17][CH2:18][CH2:19][C:20]#[N:21].C(=O)([O-])[O-].[Na+].[Na+]>CC(C)CC(=O)C.[I-].[K+]>[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:14][CH2:13][N:12]([CH2:16][CH2:17][CH2:18][CH2:19][C:20]#[N:21])[CH2:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 804745-ChlorovaleronitrileHCID 936011-(3,4-Dichlorophenyl)piperazine

Produkt 1

HCID 219996984-(3,4-Dichlorophenyl)-1-piperazinepentanenitrileAusbeute 72,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 4875Potassium IodideKatalysatorHCID 7909Methyl Isobutyl KetoneLösungsmittel

Versuchsvorschrift

A mixture of 1-(3,4-dichlorophenyl)piperazine (0.1 mol), 5-chloropentanenitrile (0.13 mol), sodium carbonate (10 g) and potassium iodide (0.1 g) in 4-methyl-2-pentanone (280 ml) was stirred and refluxed for 10 hours. The reaction mixture was cooled, filtered and the filtrate was evaporated. 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, yielding 22.5 g (72%) of 4-(3,4-dichlorophenyl)-1-piperazinepentanenitrile (interm. 2).

Aufarbeitung

  1. temperaturerefluxed for 10 hours
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltered
  4. customthe filtrate was evaporated
  5. customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH 95/5)
  6. customThe pure fractions were collected
  7. customthe solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-4a5bdc30be874aee83bdc8629aaa3da8
Quelldatensatz
uspto-grants-2001_05
Patentnummer
US06224849B1

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