1-Methyl-4-[2-nitro-4-(trifluoromethyl)phenyl]piperazine → 2-(4-Methylpiperazin-1-yl)-5-(trifluoromethyl)aniline

HRID 446245Notes

Reaction equation

HRID 446245 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][C:9]=2[N+:18]([O-])=O)[CH2:4][CH2:3]1>CO.[Pd]>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:15])[F:16])=[CH:10][C:9]=2[NH2:18])[CH2:6][CH2:7]1

Participants

4

Reactant 1

HCID 28607241-Methyl-4-[2-nitro-4-(trifluoromethyl)phenyl]piperazine

Product 1

HCID 6932882-(4-Methylpiperazin-1-yl)-5-(trifluoromethyl)aniline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To 1-Methyl-4-(2-nitro-4-trifluoromethyl-phenyl)-piperazine (1.46 g, 5.05 mmol) in dry MeOH (50 mL) was added Pd/C (10%, 535 mg). H2 gas was bubbled through the solution at room temperature overnight with vigorous stirring. The reaction mixture was filtered through celite to provide, after concentration, the desired product as a white solid. MS (M+H)+=260; Calc'd 259.28 for C12H16F3N3.

Workup

  1. customH2 gas was bubbled through the solution at room temperature overnight with vigorous stirring
  2. filtrationThe reaction mixture was filtered through celite
  3. customto provide
  4. concentrationafter concentration

Sources & evidence

ORD record
ord-023c91e52a0443a0a473d7f473f37923
Source dataset
uspto-grants-2013_07
Patent number
US08476434B2

Reaction notes

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