Piperazine → 4-Fluoro-2-(piperazin-1-yl)benzonitrile

HRID 849493

Reaktionsgleichung

Reaktionsgleichung von HRID 849493
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.F[C:8]1[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:9]=1[C:10]#[N:11]>CN(C)C(=O)C>[C:10]([C:9]1[CH:8]=[CH:15][C:14]([F:16])=[CH:13][C:12]=1[N:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1)#[N:11]

Komponenten

4

Edukt 2

HCID 4837PiperazineHCID 775452,4-Difluorobenzonitrile

Produkt 1

HCID 193671084-Fluoro-2-(piperazin-1-yl)benzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374DimethylacetamideLösungsmittel

Reaktionsbedingungen

Temperatur
122 °C

Versuchsvorschrift

A mixture of piperazine (Aldrich; 3.99 g), 2,4-difluorobenzonitrile, and N,N-dimethylacetamide (20 mL) is stirred for 1.5 h at 122° C. After cooling, the mixture is partitioned between dichloromethane and satd. aq. sodium bicarbonate. The organic layers are dried over magnesium sulfate and concentrated. The residue is chromatographed on silica gel and the appropriate fractions are combined and concentrated to give 1.44 g of 1(2-cyano-5-fluorophenyl)piperazine; 1H NMR (CDCl3) δ 3.01, 3.30, 6.56, 6.63, 7.40.

Aufarbeitung

  1. temperatureAfter cooling
  2. customthe mixture is partitioned between dichloromethane
  3. dry with materialThe organic layers are dried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue is chromatographed on silica gel
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-9ef007546ddc48d2936bb14ca1172ab3
Quelldatensatz
uspto-grants-2000_01
Patentnummer
US06013654

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