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

HRID 1416286

Reaktionsgleichung

Reaktionsgleichung von HRID 1416286
[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) δ3.01, 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-5980976b2f5f4071b3a4e96b7f854466
Quelldatensatz
uspto-grants-1999_06
Patentnummer
US05912246

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