Acetic Acid → HCID 68476364, compound

HRID 1802827Notes

Reaction equation

HRID 1802827 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

HCID 68476364HCID 68476364, compoundYield 86.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-7d6ff5c4580a42dc995ae346e28f01d0
Source dataset
uspto-grants-2013_01
Patent number
US08349885B2

Reaction notes

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