HCID 21701698, compound → HCID 21701687, compound

HRID 1596235Notes

Reaction equation

HRID 1596235 reaction equation
[N+:1]([C:4]1[CH:27]=[CH:26][C:7]([C:8]([N:10]2[CH2:15][CH2:14][N:13]([NH:16][C:17](=[O:25])[C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)[CH2:12][CH2:11]2)=[O:9])=[CH:6][CH:5]=1)([O-])=O>[Pd].CO>[NH2:1][C:4]1[CH:27]=[CH:26][C:7]([C:8]([N:10]2[CH2:15][CH2:14][N:13]([NH:16][C:17](=[O:25])[C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)[CH2:12][CH2:11]2)=[O:9])=[CH:6][CH:5]=1

Participants

4

Reactant 1

HCID 21701698HCID 21701698, compound

Product 1

HCID 21701687HCID 21701687, compoundYield 80.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

N-[4-(4-Nitrobenzoyl)-1-piperazinyl]-4-fluorobenzamide (254 mg) was hydrogenated over 10% palladium on carbon (73 mg) in methanol (10 ml) at ambient temperature for 4 hours. The catalyst was filtered off over Celite pad and the filtrate was concentrated in vacuo to give crystals. The crystals were recrystallized from methanol, ethyl acetate and n-hexane to give N-[4-(4-aminobenzoyl)-1-piperazinyl]-4-fluorobenzamide (188 mg).

Workup

  1. filtrationThe catalyst was filtered off over Celite pad
  2. concentrationthe filtrate was concentrated in vacuo
  3. customto give crystals
  4. customThe crystals were recrystallized from methanol, ethyl acetate and n-hexane

Sources & evidence

ORD record
ord-4db06849a67340808bd1d4bc08da16f2
Source dataset
uspto-grants-2001_09
Patent number
US06291464B1

Reaction notes

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