Toluene → 1-(Pyridin-3-yl)piperazine

HRID 564877

Reaktionsgleichung

Reaktionsgleichung von HRID 564877
Br[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.[NH:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1.CC(C)([O-])C.[Na+].C1(C)C=CC=CC=1>O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1C=CC(P(C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[N:4]1[CH:5]=[CH:6][CH:7]=[C:2]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH:3]=1

Komponenten

8

Edukt 4

HCID 1140TolueneHCID 4837PiperazineHCID 122863-BromopyridineHCID 23676156Sodium t-butoxide

Produkt 1

HCID 4372341-(Pyridin-3-yl)piperazineAusbeute 29 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 634876Binap, (A+-)-KatalysatorHCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 1.0 g (6.3 mmol) of 3-bromopyridine, 2.2 g (25 mmol) of piperazine, 16 mg of tris(dibenzylideneacetone)-dipalladium(0), 32 mg of (S)-(−)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl, 1.3 g (13.4 mmol) of sodium t-butoxide, and 50 ml of toluene was heated under reflux for 24 hours in a nitrogen atmosphere. The reaction mixture was diluted with water and extracted with chloroform. The combined organic layer was washed with a saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate. The solvent was evaporated off, and the residue was purified by silica gel column chromatography using a 9:1 mixture of chloroform and methanol as a developing solvent to give 0.27 g (29%) of the title compound.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux for 24 hours in a nitrogen atmosphere
  3. extractionextracted with chloroform
  4. washThe combined organic layer was washed with a saturated sodium chloride aqueous solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated off
  7. customthe residue was purified by silica gel column chromatography
  8. additiona 9:1 mixture of chloroform and methanol as a developing solvent

Quellen und Nachweise

ORD-Eintrag
ord-c4240a151e8047849a417902692f5887
Quelldatensatz
uspto-grants-2001_01
Patentnummer
US06169086A

Verknüpfte Notizen

Wird geladen…