Water → 5-[1-(2-Thienylcarbonyl)-4-piperidyloxy]imidazo[1,2-a]pyridine

HRID 1081742Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1081742
[H-].[Na+].[S:3]1[CH:7]=[CH:6][CH:5]=[C:4]1[C:8]([N:10]1[CH2:15][CH2:14][CH:13]([OH:16])[CH2:12][CH2:11]1)=[O:9].Cl[C:18]1[N:23]2[CH:24]=[CH:25][N:26]=[C:22]2[CH:21]=[CH:20][CH:19]=1.O>CN(C)C=O.C(OCC)(=O)C>[S:3]1[CH:7]=[CH:6][CH:5]=[C:4]1[C:8]([N:10]1[CH2:11][CH2:12][CH:13]([O:16][C:18]2[N:23]3[CH:24]=[CH:25][N:26]=[C:22]3[CH:21]=[CH:20][CH:19]=2)[CH2:14][CH2:15]1)=[O:9]

Komponenten

7

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 109537225-Chloroimidazo[1,2-A]pyridineHCID 23362856(4-Hydroxypiperidin-1-yl)(thiophen-2-yl)methanone

Produkt 1

HCID 233629645-[1-(2-Thienylcarbonyl)-4-piperidyloxy]imidazo[1,2-a]pyridineAusbeute 4,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a suspension of 60% sodium hydride in oil (0.40 g, 10 mmoles) in dimethylformamide (30 ml) was added 1-(2-thienylcarbonyl)-4-hydroxypiperidine (2.11 g, 10 mmoles) with stirring under ice-cooling and the mixture was stirred at room temperature for 30 minutes. To this reaction mixture was added 5-chloroimidazo[1,2-a]pyridine (1.53 g, 10 mmoles) with stirring under ice-cooling, followed by stirring at room temperature for 7 hours. Water was added to the reaction mixture, which was extratced with ethyl acetate and dried. After the solvent was distilled off, the residue was purified with column chromatography [eluent:ethyl acetate/hexane (1:1)→ethyl acetate/hexane (2:1)→ethyl acetate/ethanol (50:1)] to obtain 0.15 g of the desired product (4.6%, pale yellow oily product).

Aufarbeitung

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 30 minutes
  3. stirringwith stirring under ice-
  4. temperaturecooling
  5. stirringby stirring at room temperature for 7 hours
  6. customdried
  7. distillationAfter the solvent was distilled off
  8. customthe residue was purified with column chromatography [eluent:ethyl acetate/hexane (1:1)→ethyl acetate/hexane (2:1)→ethyl acetate/ethanol (50:1)]

Quellen und Nachweise

ORD-Eintrag
ord-a1c10cd6dc674f42964146e24d155097
Quelldatensatz
uspto-grants-1996_12
Patentnummer
US05587383

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