Piperidine → (1E,6E)-1-(1H-indol-6-yl)-7-[2-methoxy-4-[(4-methylpiperazin-1-yl)methyl]phenyl]hepta-1,6-diene-3,5-dione

HRID 632508

Reaktionsgleichung

Reaktionsgleichung von HRID 632508
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7](/[CH:10]=[CH:11]/[C:12](=[O:17])[CH2:13][C:14](=[O:16])[CH3:15])[CH:8]=2)[CH:3]=[CH:2]1.[B]=O.[CH3:20][O:21][C:22]1[CH:29]=[C:28]([CH2:30][N:31]2[CH2:36][CH2:35][N:34]([CH3:37])[CH2:33][CH2:32]2)[CH:27]=[CH:26][C:23]=1[CH:24]=O.N1CCCCC1.C([O-])([O-])=O.[K+].[K+]>CCOC(C)=O.B(OC(C)C)(OC(C)C)OC(C)C>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7](/[CH:10]=[CH:11]/[C:12](=[O:17])[CH2:13][C:14](=[O:16])/[CH:15]=[CH:24]/[C:23]3[CH:26]=[CH:27][C:28]([CH2:30][N:31]4[CH2:36][CH2:35][N:34]([CH3:37])[CH2:33][CH2:32]4)=[CH:29][C:22]=3[O:21][CH3:20])[CH:8]=2)[CH:3]=[CH:2]1

Komponenten

8

Edukt 5

HCID 8082PiperidineHCID 11430Potassium CarbonateHCID 6327189Boron monoxideHCID 67107107(E)-6-(1H-indol-6-yl)hex-5-ene-2,4-dioneHCID 897259352-Methoxy-4-[(4-methylpiperazin-1-yl)methyl]benzaldehyde

Produkt 1

HCID 117888920(1E,6E)-1-(1H-indol-6-yl)-7-[2-methoxy-4-[(4-methylpiperazin-1-yl)methyl]phenyl]hepta-1,6-diene-3,5-dioneAusbeute 47 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittel3×HCID 21531Triisopropyl borateLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To 200 mL of a solution of 7.56 g of (E)-6-(1H-indol-6-yl)hex-5-ene-2,4-dione in AcOEt was added 3.24 g of boron oxide, and the mixture was stirred at 70° C. for 1 hour. To this, 15 mL of a solution of 8.68 g of 2-methoxy-4-[(4-methylpiperazin-1-yl)methyl]benzaldehyde in AcOEt and 18.3 mL of triisopropyl borate were successively added, and the mixture was stirred at the same temperature for 40 minutes. Then, 10 mL of a solution of 0.35 mL of piperidine in AcOEt was added. The mixture was stirred at 70° C. for 3 hours and was allowed to cool back to room temperature. To the reaction mixture, 100 mL of a 10% K2CO3 aqueous solution was added, and the mixture was stirred for 1 hour. The organic layer was separated and concentrated. The residue was purified by amino-silica gel column chromatography (heptane/AcOEt system) to give 7.14 g of the title compound (47% yield).

Aufarbeitung

  1. stirringthe mixture was stirred at the same temperature for 40 minutes
  2. stirringThe mixture was stirred at 70° C. for 3 hours
  3. temperatureto cool back to room temperature
  4. stirringthe mixture was stirred for 1 hour
  5. customThe organic layer was separated
  6. concentrationconcentrated
  7. customThe residue was purified by amino-silica gel column chromatography (heptane/AcOEt system)

Quellen und Nachweise

ORD-Eintrag
ord-6c3f5b8b953d485fa46bb925ca4d01c1
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09321752B2

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