3-Fluoro-4-(4-{2-methoxyethyl}-3-oxopiperazin-1-yl)nitrobenzene → 5-Amino-2-(4-{2-methoxyethyl}-3-oxopiperazin-1-yl)fluorobenzene

HRID 1108586Notes

Reaction equation

HRID 1108586 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N+:19]([O-])=O)[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][O:16][CH3:17])[C:10](=[O:18])[CH2:9]1>C(OCC)(=O)C.CN(C=O)C>[NH2:19][C:4]1[CH:5]=[CH:6][C:7]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][O:16][CH3:17])[C:10](=[O:18])[CH2:9]2)=[C:2]([F:1])[CH:3]=1

Participants

4

Reactant 1

HCID 187839133-Fluoro-4-(4-{2-methoxyethyl}-3-oxopiperazin-1-yl)nitrobenzene

Product 1

HCID 187839025-Amino-2-(4-{2-methoxyethyl}-3-oxopiperazin-1-yl)fluorobenzene

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-Fluoro-4-(4-{2-methoxyethyl}-3-oxopiperazin-1-yl)nitrobenzene (4 g) was dissolved in a mixture of ethyl acetate (200 ml) and DMF (5 ml), and the solution flushed with argon. Palladium (10% on carbon, 200 mg) was added, and the mixture hydrogenated under ambient pressure. After gas uptake had ceased, the mixture was filtered through celite and solvent was evaporated to give 5-amino-2-(4-{2-methoxyethyl}-3-oxopiperazin-1-yl)fluorobenzene which was used without further purification.

Workup

  1. customthe solution flushed with argon
  2. additionPalladium (10% on carbon, 200 mg) was added
  3. filtrationthe mixture was filtered through celite and solvent
  4. customwas evaporated

Sources & evidence

ORD record
ord-63c82f0e59394599b174afcc46c6e44e
Source dataset
uspto-grants-2000_05
Patent number
US06069145

Reaction notes

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