Water → 1-(3,4-dihydroquinolin-1(2H)-ylmethyl)-4-propylpyrrolidin-2-one

HRID 2043659Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2043659
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.[H-].[Na+].Cl[CH2:14][N:15]1[CH2:19][CH:18]([CH2:20][CH2:21][CH3:22])[CH2:17][C:16]1=[O:23].O>CN(C=O)C>[N:1]1([CH2:14][N:15]2[CH2:19][CH:18]([CH2:20][CH2:21][CH3:22])[CH2:17][C:16]2=[O:23])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 694601,2,3,4-TetrahydroquinolineHCID 536292161-(Chloromethyl)-4-propylpyrrolidin-2-one

Produkt 1

HCID 577430341-(3,4-dihydroquinolin-1(2H)-ylmethyl)-4-propylpyrrolidin-2-oneAusbeute 28 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

To a solution of 1,2,3,4-tetrahydroquinoline x158 (400 mg, 3 mmol, 1 eq) in DMF (7 ml) maintained under argon is added NaH (60% in mineral oil; 120 mg, 3 mmol, 1 eq). The reaction mixture is stirred for three hour at room temperature, then a solution of 1-(chloromethyl)-4-propylpyrrolidin-2-one x63 in DMF (1 M, 3 ml, 3 mmol, 1 eq) is added. The reaction mixture is stirred for 20 hours at the same temperature. Water (70 ml) is added and the resulting mixture is extracted with ethyl acetate (30 ml). The organic phase is washed twice with water and dried over Na2SO4. After filtration and evaporation, the crude product is purified by two consecutive chromatographies on silicagel (CH2Cl2/MeOH gradient, then CH2Cl2). Pure 1-(3,4-dihydroquinolin-1(2H)-ylmethyl)-4-propylpyrrolidin-2-one 295 is obtained as syrup (231 mg).

Aufarbeitung

  1. stirringThe reaction mixture is stirred for 20 hours at the same temperature
  2. extractionthe resulting mixture is extracted with ethyl acetate (30 ml)
  3. washThe organic phase is washed twice with water
  4. dry with materialdried over Na2SO4
  5. filtrationAfter filtration and evaporation
  6. customthe crude product is purified by two consecutive chromatographies on silicagel (CH2Cl2/MeOH gradient

Quellen und Nachweise

ORD-Eintrag
ord-f914a393db4943759e4ce5fd90e9a0c5
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08586623B2

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