Reaktion #44130

Reaktionsgleichung

(2R)-2-Methylpiperazine

caesium carbonate

2,2′-bis(diphenylphosphino)-1,1′-binaphthyl

2-methyl-5-quinolinyl trifluoromethanesulfonate

2-Methyl-5-quinolinyl trifluoromethanesulfonate

→

title compound

Ausbeute 58.0%

2-Methyl-5-[(3R)-3-methyl-1-piperazinyl]quinoline

Ausbeute 58.0%

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturat reflux under nitrogen for 3 hours
2. 2
   Sonstigequenched
3. 3
   Extraktionextracted with ethyl acetate (3×20 mL)
4. 4
   Trocknendried over sodium sulfate
5. 5
   Einengenconcentrated under reduced pressure
6. 6
   SonstigeThe crude was purified by flash chromatography on silica gel
7. 7
   Wascheneluting with dichloromethane-methanol (95:5)

Vorschrift

(2R)-2-Methylpiperazine (0.550 g; 2 eq), caesium carbonate (1.78 g; 2 eq), palladium acetate (0.123 g; 0.2 eq) and 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (0.513 g; 0.3 eq) were added to a solution of 2-methyl-5-quinolinyl trifluoromethanesulfonate (D1) (0.8 g; 1 eq) in toluene (30 mL) under an inert atmosphere. The reaction mixture was stirred at reflux under nitrogen for 3 hours. The reaction cooled to room temperature, quenched using saturated aqueous ammonium chloride solution (15 mL) and extracted with ethyl acetate (3×20 mL). The organic layers were combined, dried over sodium sulfate and concentrated under reduced pressure. The crude was purified by flash chromatography on silica gel, eluting with dichloromethane-methanol (95:5) affording the title compound in 58% yield (0.383 g).

Quelle