Triethylamine → 4,5-Dihydro-4-(1-tert-butoxycarbonylpiperidin-4-ylmethyl)-3H-1,4,8b-triazaacenaphthylen-3-one

HRID 1068777Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1068777
[C:1]([C:6]1[N:10]2[C:11]([CH2:15]Cl)=[CH:12][CH:13]=[CH:14][C:9]2=[N:8][CH:7]=1)([O:3]CC)=O.[C:17]([O:21][C:22]([N:24]1[CH2:29][CH2:28][CH:27]([CH2:30][NH2:31])[CH2:26][CH2:25]1)=[O:23])([CH3:20])([CH3:19])[CH3:18].C(N(CC)CC)C>C(O)C>[C:17]([O:21][C:22]([N:24]1[CH2:29][CH2:28][CH:27]([CH2:30][N:31]2[CH2:15][C:11]3[N:10]4[C:6](=[CH:7][N:8]=[C:9]4[CH:14]=[CH:13][CH:12]=3)[C:1]2=[O:3])[CH2:26][CH2:25]1)=[O:23])([CH3:20])([CH3:19])[CH3:18]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 7368171-Boc-4-(aminomethyl)piperidineHCID 108575483-Carbethoxy-5-chloromethylimidazo[1,2-a]pyridine

Produkt 1

HCID 99074084,5-Dihydro-4-(1-tert-butoxycarbonylpiperidin-4-ylmethyl)-3H-1,4,8b-triazaacenaphthylen-3-oneAusbeute 72,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution prepared by dissolving 5.78 g (24.22 mM) of 3-carbethoxy-5-chloromethylimidazo[1,2-a]pyridine, 7.78 g (36.33 mM) of 1-tert-butoxycarbonyl-4-aminomethylpiperidine, and 6.75 ml (48.44 mM) of triethylamine in 100 ml of ethanol was refluxed under argon gas for 3 hours. After completion of the reaction, the solvent was distilled off under reduced pressure and the residue was extracted with 100 ml of chloroform. The organic layer was washed with saturated aqueous NaCl solution and dried over MgSO4 and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluent: chloroform-methanol=20:1) to provide 6.50 g (yield 72.4%) of the title compound as yellow liquid.

Aufarbeitung

  1. customA solution prepared
  2. temperaturewas refluxed under argon gas for 3 hours
  3. customAfter completion of the reaction
  4. distillationthe solvent was distilled off under reduced pressure
  5. extractionthe residue was extracted with 100 ml of chloroform
  6. washThe organic layer was washed with saturated aqueous NaCl solution
  7. dry with materialdried over MgSO4
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (eluent: chloroform-methanol=20:1)

Quellen und Nachweise

ORD-Eintrag
ord-ec414644e40148978853f88e11f62249
Quelldatensatz
uspto-grants-2001_06
Patentnummer
US06251905B1

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