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

HRID 1802827Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1802827
[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+]>ClCCl.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 6344DichloromethaneLösungsmittel

Versuchsvorschrift

5-Chloro-3-formyl-7-nitro-2-phenyl-1H-indole (0.5 g, 1.66 mmol) obtained in Step 1 was dissolved in dichloromethane (20 mL), and thereto acetic acid (0.10 g, 1.66 mmol), 2-oxopiperazine (0.3 g, 3.32 mmol) and sodium triacetoxy borohydride (0.71 g, 3.32 mmol) were added in drops. The mixture was stirred at room temperature for 4 hours. At the end of reaction, the mixture was diluted with water, and extracted with dichloromethane. The extract was washed with saturated sodium chloride solution, dried over anhydrous magnesium sulfate and filtered. The solvent was removed under reduced pressure and the residue was separated by column chromatography to give 5-chloro-7-nitro-3-(2-oxo-piperazin-4-yl)methyl-2-phenyl-1H-indole (0.55 g, Yield 86%).

Aufarbeitung

  1. customAt the end of reaction
  2. extractionextracted with dichloromethane
  3. washThe extract was washed with saturated 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 separated by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-7d6ff5c4580a42dc995ae346e28f01d0
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08349885B2

Notizen zur Reaktion

Wird geladen…