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

HRID 56104Notes

Reaction equation

HRID 56104 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>C1COCC1.[Pd]>[F:1][C:2]1[CH:7]=[C:6]([CH:5]=[CH:4][C:3]=1[N:11]1[CH2:12][CH2:13][N:14]([CH3:17])[CH2:15][CH2:16]1)[NH2:8]

Participants

4

Reactant 1

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

Product 1

HCID 27830553-Fluoro-4-(4-methylpiperazin-1-yl)aniline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(2-fluoro-4-nitrophenyl)-4-methylpiperazine (14.76 g, 61.70 mmol) in THF (80 mL) was added Pd/C (3.00 g). The reaction was stirred at rt under H2 overnight. The mixture was filtered, and the filtrate was concentrated in vacuo to give the title compound as an offwhite solid (11.99 g, 93%).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-0fd3850b60ba41a8a1fbd3bae9cfd44e
Source dataset
uspto-grants-2016_09
Patent number
US09434695B2

Reaction notes

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