Potassium Carbonate → 2-[4-(Cyclohexylmethyl)piperazin-1-yl]quinoline-3-carbaldehyde

HRID 577779

Reaktionsgleichung

Reaktionsgleichung von HRID 577779
[CH:1]1([CH2:7][N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl[C:15]1[C:24]([CH:25]=[O:26])=[CH:23][C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[CH:1]1([CH2:7][N:8]2[CH2:9][CH2:10][N:11]([C:15]3[C:24]([CH:25]=[O:26])=[CH:23][C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[N:16]=3)[CH2:12][CH2:13]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 6909582-Chloro-3-quinolinecarboxaldehydeHCID 27358851-(Cyclohexylmethyl)piperazine

Produkt 1

HCID 574868172-[4-(Cyclohexylmethyl)piperazin-1-yl]quinoline-3-carbaldehydeAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

1-(Cyclohexylmethyl)piperazine (0.42 mL, 2.2 mmol) was added to a mixture of 2-chloro-3-quinolinecarboxaldehyde (0.383 g, 2.0 mmol) and potassium carbonate (0.7 g, 5.0 mmol) in anhydrous DMF (4 mL) at ambient temperature under a nitrogen atmosphere. After being stirred for 20 minutes, the reaction mixture was heated at 110° C. for 4.5 h. After cooling to room temperature this mixture was diluted with water (40 mL) and extracted with ethyl acetate (3×30 mL). The combined organic extracts were washed with brine, dried over sodium sulfate, filtered, and then concentrated under vacuum to give a pale brown crude product. Purification by silica gel column chromatography and eluting with 2.5% methanol in dichloromethane afforded the title compound (0.56 g), yield: 86%.

Aufarbeitung

  1. temperatureAfter cooling to room temperature this mixture
  2. extractionextracted with ethyl acetate (3×30 mL)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customto give a pale brown crude product
  8. customPurification by silica gel column chromatography
  9. washeluting with 2.5% methanol in dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-596641ef58e540a4a5d550a7168db462
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09040558B2

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