Potassium Carbonate → 1-Benzyl-1'-[(4-cyclobutylpiperazin-1-yl)carbonyl]spiro[indole-3,4'-piperidin]-2(1H)-one

HRID 2262731Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2262731
[CH2:1]([N:8]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:10]2([CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)[C:9]1=[O:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC(OC1C=CC([N+]([O-])=O)=CC=1)=O.[C:36]([O-:39])([O-])=O.[K+].[K+].[CH:42]1([N:46]2[CH2:51][CH2:50][NH:49][CH2:48][CH2:47]2)[CH2:45][CH2:44][CH2:43]1>CC#N>[CH2:1]([N:8]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:10]2([CH2:11][CH2:12][N:13]([C:36]([N:49]3[CH2:50][CH2:51][N:46]([CH:42]4[CH2:45][CH2:44][CH2:43]4)[CH2:47][CH2:48]3)=[O:39])[CH2:14][CH2:15]2)[C:9]1=[O:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 11430Potassium CarbonateHCID 821294-Nitrophenyl chloroformateHCID 47386021-CyclobutylpiperazineHCID 497602201-Benzylspiro[indole-3,4'-piperidin]-2(1H)-one

Produkt 1

HCID 575138781-Benzyl-1'-[(4-cyclobutylpiperazin-1-yl)carbonyl]spiro[indole-3,4'-piperidin]-2(1H)-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel2×

Versuchsvorschrift

A suspension of 1-benzylspiro[indole-3,4′-piperidin]-2(1H)-one (0.417 mmol), 4-nitrophenyl chloroformate (84 mg, 0.417 mmol) and K2CO3 (172 mg, 1.25 mmol) in CH3CN (6 ml) is stirred at ambient temperature for 2 h. A solution of 1-cyclobutylpiperazine (0.417 mmol) and TEA (0.175 ml, 1.25 mmol) in CH3CN (4 ml) is added and the mixture is heated at 110° C. in a sealed tube overnight. Solvent is removed in vacuo and to the residue is added EtOAc (15 ml). The mixture is stirred at rt for 15 min and filtered. The filtrated is evaporated and the residue is purified by PTLC to give the title compound as a white solid. LC-MS (M+1): 458.3.

Aufarbeitung

  1. temperaturethe mixture is heated at 110° C. in a sealed tube overnight
  2. customSolvent is removed in vacuo and to the residue
  3. additionis added EtOAc (15 ml)
  4. stirringThe mixture is stirred at rt for 15 min
  5. filtrationfiltered
  6. customThe filtrated is evaporated
  7. customthe residue is purified by PTLC

Quellen und Nachweise

ORD-Eintrag
ord-fd9a610642864ff5a3aef4996fe75504
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07851474B2

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