3-Fluoro-4-(4-methyl-3-oxopiperazin-1-yl)nitrobenzene → 4-(4-Amino-2-fluorophenyl)-1-methylpiperazin-2-one

HRID 1108569Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([N+:16]([O-])=O)[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:13][CH2:12][N:11]([CH3:14])[C:10](=[O:15])[CH2:9]1>CN(C=O)C.CO>[NH2:16][C:4]1[CH:5]=[CH:6][C:7]([N:8]2[CH2:13][CH2:12][N:11]([CH3:14])[C:10](=[O:15])[CH2:9]2)=[C:2]([F:1])[CH:3]=1

Participants

Conditions

Temperature: 5 °C

Procedure

3-Fluoro-4-(4-methyl-3-oxopiperazin-1-yl)nitrobenzene (3.33 g) was dissolved in a mixture of DMF (40 ml) and methanol (10 ml), and the solution flushed with argon. Ammonium formate (4.15 g) was added, and the mixture cooled to 5° C. Palladium (10% on carbon, 104 mg) was added, and the temperature allowed to rise to ambient as the mixture was stirred under argon for 2 hours. Solvents were evaporated to give an air sensitive product, 5-amino-2-(4-methyl-3-oxopiperazin-1-yl)fluorobenzene, which was used as such in the next stage.

Workup

customthe solution flushed with argon
additionAmmonium formate (4.15 g) was added
additionPalladium (10% on carbon, 104 mg) was added
customSolvents were evaporated

Sources & evidence

ORD record: ord-4deda534d3a54a0cba08fba9211803a3
Source dataset: uspto-grants-2000_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06069145

Reaction notes

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