Piperazine → 1-(Pyridin-3-yl)piperazine

HRID 583599

Reaktionsgleichung

Reaktionsgleichung von HRID 583599
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Br[C:8]1[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=1>CC1C=CC=CC=1C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[N:10]1[CH:11]=[CH:12][CH:13]=[C:8]([N:1]2[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]2)[CH:9]=1

Komponenten

5

Edukt 2

HCID 4837PiperazineHCID 122863-Bromopyridine

Produkt 1

HCID 4372341-(Pyridin-3-yl)piperazineAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 7237O-XyleneLösungsmittel4×

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A 200 ml Kjeldahl flask equipped with a cooling condenser and a thermometer was charged with a solution of 22 g of piperazine in 20 ml of o-xylene, a solution of 6.72 g of 3-bromopyridine in 20 ml of o-xylene and a solution of 5.66 g of NaOBut in 20 ml of o-xylene, and further with a solution of 48 mg of palladium acetate in 15 ml of o-xylene (the ratio of palladium atom/heterocyclic aromatic halide=0.5% by mole). The flask was flushed with nitrogen for about 20 minutes while the content was stirred, and 0.2 ml of tri-tert.-butylphosphine was added. Then the mixture was heated to 120° C., and maintained at that temperature for 3 hours with stirring. After completion of the reaction, the same treatment as employed in Example 1 was conducted to give colorless oily 1-(3-pyridyl)piperazine. The yield was 86% by mole.

Aufarbeitung

  1. customA 200 ml Kjeldahl flask equipped with a cooling condenser
  2. customThe flask was flushed with nitrogen for about 20 minutes while the content
  3. addition0.2 ml of tri-tert.-butylphosphine was added
  4. temperaturemaintained at that temperature for 3 hours
  5. stirringwith stirring
  6. customAfter completion of the reaction

Quellen und Nachweise

ORD-Eintrag
ord-33124133cff348b497579152f75ba0e5
Quelldatensatz
uspto-grants-1999_07
Patentnummer
US05929281

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