Acetic Acid → 5-Chloro-7-nitro-3-(2-oxo-piperazin-4-yl)methyl-2-phenyl-1H-indole

HRID 2089567Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2089567
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([N+:11]([O-:13])=[O:12])[CH:10]=1)[NH:7][C:6]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[C:5]2[CH:20]=O.C(O)(=O)C.[O:26]=[C:27]1[CH2:32][NH:31][CH2:30][CH2:29][NH:28]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C.O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([N+:11]([O-:13])=[O:12])[CH:10]=1)[NH:7][C:6]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[C:5]2[CH2:20][N:31]1[CH2:30][CH2:29][NH:28][C:27](=[O:26])[CH2:32]1

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 231360Piperazin-2-oneHCID 5049666Sodium triacetoxyborohydrideHCID 866438345-Chloro-3-formyl-7-nitro-2-phenyl-1H-indole

Produkt 1

HCID 684763645-Chloro-7-nitro-3-(2-oxo-piperazin-4-yl)methyl-2-phenyl-1H-indoleAusbeute 86,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 63651,1-DichloroethaneLösungsmittel

Versuchsvorschrift

5-Chloro-3-formyl-7-nitro-2-phenyl-1H-indole (0.5 g, 1.66 mmol) prepared in Step A was dissolved in dichloroethane (20 mL). Acetic acid (0.10 g, 1.66 mmol), 2-oxopiperazine (0.3 g, 3.32 mmol) and sodium triacetoxyborohydride (0.71 g, 3.32 mmol) were added in drops thereto, and the mixture was stirred for 4 h at room temperature. After completion of the reaction, the reaction mixture was diluted with water, extracted with dichloromethane, washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and filtered. The solvent was removed under reduced pressure, and the residue was purified by column chromatography to give the title compound (0.55 g, Yield 86%).

Aufarbeitung

  1. customAfter completion of the reaction
  2. extractionextracted with dichloromethane
  3. washwashed with saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customThe solvent was removed under reduced pressure
  7. customthe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-2b1baf304c0f44929a6d0ffbeee4dcb0
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08436038B2

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