Triethylamine → 4,5-Dihydro-4-[3-(1-tert-butoxycarbonylpiperidin-4-yl)propan-1-yl]-3H-1,4,8b-triazaacenaphthylen-3-one

HRID 1068779Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1068779
S(O)(O)(=O)=O.[C:6]([C:11]1[N:15]2[C:16]([CH2:20]Cl)=[CH:17][CH:18]=[CH:19][C:14]2=[N:13][CH:12]=1)([O:8]CC)=O.[C:22]([O:26][C:27]([N:29]1[CH2:34][CH2:33][CH:32]([CH2:35][CH2:36][CH2:37][NH2:38])[CH2:31][CH2:30]1)=[O:28])([CH3:25])([CH3:24])[CH3:23].C(N(CC)CC)C>C(O)C>[C:22]([O:26][C:27]([N:29]1[CH2:34][CH2:33][CH:32]([CH2:35][CH2:36][CH2:37][N:38]2[CH2:20][C:16]3[N:15]4[C:11](=[CH:12][N:13]=[C:14]4[CH:19]=[CH:18][CH:17]=3)[C:6]2=[O:8])[CH2:31][CH2:30]1)=[O:28])([CH3:25])([CH3:24])[CH3:23]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 22990164tert-Butyl 4-(3-aminopropyl)piperidine-1-carboxylateHCID 702111023-Carbethoxy-5-chloromethylimidazo[1,2-a]pyridine sulfate

Produkt 1

HCID 211902104,5-Dihydro-4-[3-(1-tert-butoxycarbonylpiperidin-4-yl)propan-1-yl]-3H-1,4,8b-triazaacenaphthylen-3-oneAusbeute 62,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution prepared by dissolving 3.59 g (10.66 mM) of 3-carbethoxy-5-chloromethylimidazo[1,2-a]pyridine sulfate, 3.10 g (12.79 mM) of 3-(1-tert-butoxycarbonylpiperidin-4-yl)-1-propylamine, and 5.94 ml (42.64 mM) of triethylamine in 30 ml of ethanol was refluxed for 5 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 100 ml of 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=50:1) to provide 2.55 g (yield 62.1%) of the title compound as yellow oil.

Aufarbeitung

  1. customA solution prepared
  2. temperaturewas refluxed for 5 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 100 ml of 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=50:1)

Quellen und Nachweise

ORD-Eintrag
ord-64254b812252404dbeba8050f6c8f2f1
Quelldatensatz
uspto-grants-2001_06
Patentnummer
US06251905B1

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