1-(2-Fluoro-4-nitrophenyl)-4-methylpiperazine → 3-Fluoro-4-(4-methylpiperazin-1-yl)aniline

HRID 353714Notes

Reaction equation

HRID 353714 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[N:11]1[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]1>C(OCC)(=O)C.C(O)C.[Pd]>[F:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[CH:4][C:3]=1[N:11]1[CH2:12][CH2:13][N:14]([CH3:17])[CH2:15][CH2:16]1

Participants

5

Reactant 1

HCID 27830541-(2-Fluoro-4-nitrophenyl)-4-methylpiperazine

Product 1

HCID 27830553-Fluoro-4-(4-methylpiperazin-1-yl)anilineYield 93%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1-(2-fluoro-4-nitrophenyl)-4-methylpiperazine (5.00 g, 20.9 mmol) (from Step A above) and 10% palladium-on-carbon (0.20 g, 0.2 mmol) in ethyl acetate (100 mL) and ethanol (50 mL) was hydrogenated at 50 psi in a Parr shaker for 4 h. The mixture was filtered through Celite™. The Celite™ was washed with ethyl acetate (50 mL) and the solvent was evaporated to give 3-fluoro-4-(4-methyl-1-piperazinyl)benzenamine as a white solid (4.05 g, 93%, mp 89-91° C.).

Workup

  1. filtrationThe mixture was filtered through Celite™
  2. washThe Celite™ was washed with ethyl acetate (50 mL)
  3. customthe solvent was evaporated

Sources & evidence

ORD record
ord-40ccea2273bd466c8a75b6bd9a65e458
Source dataset
uspto-grants-2004_06
Patent number
US06756374B2

Reaction notes

Loading…