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4-[1-(3-Nitro-2-pyridyl)piperazin-4-yl-carbonyl]benzoic acid methyl ester → HCID 11110580, compound

HRID 582292
Notes
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Reaction equation

HRID 582292 reaction equation
[CH3:1][O:2][C:3](=[O:27])[C:4]1[CH:9]=[CH:8][C:7]([C:10]([N:12]2[CH2:17][CH2:16][N:15]([C:18]3[C:23]([N+:24]([O-])=O)=[CH:22][CH:21]=[CH:20][N:19]=3)[CH2:14][CH2:13]2)=[O:11])=[CH:6][CH:5]=1.[H][H]>CO.C(Cl)Cl.[Ni]>[CH3:1][O:2][C:3](=[O:27])[C:4]1[CH:9]=[CH:8][C:7]([C:10]([N:12]2[CH2:13][CH2:14][N:15]([C:18]3[C:23]([NH2:24])=[CH:22][CH:21]=[CH:20][N:19]=3)[CH2:16][CH2:17]2)=[O:11])=[CH:6][CH:5]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 118107654-[1-(3-Nitro-2-pyridyl)piperazin-4-yl-carbonyl]benzoic acid methyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 11110580HCID 11110580, compoundYield 88.1%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 887MethanolSolvent
HCID 6344
Dichloromethane
Solvent

Procedure

4-[1-(3-Nitro-2-pyridyl)piperazin-4-yl-carbonyl]benzoic acid methyl ester (5 g) was dissolved in a co-solvent of methanol (80 ml) and methylene chloride (60 ml) in a pressurized reactor. With the addition of about 1 g of Raney-nickel (50% slurry in water), the reaction mixture was filled with hydrogen gas and stirred at 50~60 psi for 4 hours. After completion of the reaction, reaction mixture was filtered through celite and filtrate was concentrated under reduced pressure. The concentrated residue was treated with hexane and ether for crystallization, filtered, washed and dried to give 4.05 g (yield: 88%) of the desired compound.

Workup

  1. customAfter completion of the reaction, reaction mixture
  2. filtrationwas filtered through celite and filtrate
  3. concentrationwas concentrated under reduced pressure
  4. additionThe concentrated residue was treated with hexane and ether for crystallization
  5. filtrationfiltered
  6. washwashed
  7. customdried

Sources & evidence

ORD record
ord-9ba848712bfb4feda5b206c85dda0741
Source dataset
uspto-grants-1999_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05922871

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes