Piperazine → 5-Chloro-2-(piperazin-1-yl)benzonitrile

HRID 849488

Reaktionsgleichung

Reaktionsgleichung von HRID 849488
Cl[C:2]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][C:3]=1[C:4]#[N:5].[NH:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1>CN(C=O)C>[Cl:10][C:7]1[CH:8]=[CH:9][C:2]([N:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)=[C:3]([CH:6]=1)[C:4]#[N:5]

Komponenten

4

Edukt 2

HCID 4837PiperazineHCID 890002,5-Dichlorobenzonitrile

Produkt 1

HCID 193671275-Chloro-2-(piperazin-1-yl)benzonitrileAusbeute 20,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 2,5-dichlorobenzonitrile (Lancaster; 2.994 g), piperazine (Aldrich; 7.616 g), and DMF (10 mL) is stirred for 4.5 h at 100° C. After cooling, the DMF is removed under reduced pressure and the residue is partitioned between dichloromethane and saturated aq. sodium bicarbonate. The organic layers are dried with MgSO4 and concentrated under reduced pressure. The residue is chromatographed on silica gel using methanol/dichloromethane (8/92) and the appropriate fractions are combined and concentrated to give 0.79 g of 5-chloro-2-(piperazin-1-yl)benzonitrile; MS m/z 221; IR (mineral oil) 1489, 802, 829, 2223, 845 cm-1, 1H NMR (CDCl3) δ 3.09, 3.18, 6.94, 7.43, 7.52.

Aufarbeitung

  1. temperatureAfter cooling
  2. customthe DMF is removed under reduced pressure
  3. customthe residue is partitioned between dichloromethane and saturated aq. sodium bicarbonate
  4. dry with materialThe organic layers are dried with MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is chromatographed on silica gel
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-22c467f1d577466d9788be631f81d645
Quelldatensatz
uspto-grants-2000_01
Patentnummer
US06013654

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