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

HRID 734491

Reaktionsgleichung

Reaktionsgleichung von HRID 734491
C(N(CC)C(C)C)(C)C.[CH3:10][C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][C:17]=2[N:21]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)[N:12]=1.CS(O[CH2:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[C:36]([N+:40]([O-:42])=[O:41])[CH:35]=1)(=O)=O>CN(C)C=O>[CH3:10][C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][C:17]=2[N:21]2[CH2:26][CH2:25][N:24]([CH2:32][CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[C:36]([N+:40]([O-:42])=[O:41])[CH:35]=3)[CH2:23][CH2:22]2)[N:12]=1

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 219738843-Nitrophenethyl methanesulfonateHCID 498519012-Methyl-5-piperazin-1-yl-quinoline

Produkt 1

HCID 498519022-Methyl-5-(4-[2-(3-nitrophenyl)ethyl]-1-piperazinyl}quinolineAusbeute 64 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

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).

Aufarbeitung

  1. concentrationThe dark solution was concentrated under reduced pressure
  2. additiondiluted with water (3 mL) and brine (1 mL)
  3. extractionextracted into ethyl acetate (3×3 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe crude was purified by flash chromatography
  7. washeluting with a gradient from dichloromethane to dichloromethane/MeOH (98/2)

Quellen und Nachweise

ORD-Eintrag
ord-92a50017c4344279b3dde71817db52b1
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07592346B2

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