Reaktion #44049

Reaktionsgleichung

N,N-Diisopropylethylamine

2-methyl-5-(1-piperazinyl)quinoline

2-Methyl-5-(1-piperazinyl)quinoline

2-(3-nitrophenyl)ethyl methanesulfonate

→

title compound

Ausbeute 64.0%

2-Methyl-5-{4-[2-(3-nitrophenyl)ethyl]-1-piperazinyl}quinoline

Ausbeute 64.0%

Lösungsmittel

dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenThe dark solution was concentrated under reduced pressure
2. 2
   workup.ADDITIONdiluted with water (3 mL) and brine (1 mL)
3. 3
   Extraktionextracted into ethyl acetate (3×3 mL)
4. 4
   Trocknendried over Na2SO4
5. 5
   Einengenconcentrated under reduced pressure
6. 6
   SonstigeThe crude was purified by flash chromatography
7. 7
   Wascheneluting with a gradient from dichloromethane to dichloromethane/MeOH (98/2)

Vorschrift

N,N-Diisopropylethylamine (0.8 mL; 5 eq) was added to a solution of 2-methyl-5-(1-piperazinyl)quinoline (D3) (0.2 g; 1 eq) and 2-(3-nitrophenyl)ethyl methanesulfonate (D4) (0.22; 1 eq) in dimethylformamide (1.5 mL). The reaction mixture was heated to 100° C. for 10 hours. The dark solution was concentrated under reduced pressure, diluted with water (3 mL) and brine (1 mL) and extracted into ethyl acetate (3×3 mL). The organic layers were combined, dried over Na2SO4 and concentrated under reduced pressure. The crude was purified by flash chromatography, eluting with a gradient from dichloromethane to dichloromethane/MeOH (98/2) affording the title compound in 64% yield (0.21 g).

Quelle