1-Methyl-4-[[3-nitro-5-(trifluoromethyl)phenyl]methyl]piperazine → 3-((4-Methylpiperazin-1-yl)methyl)-5-(trifluoromethyl)aniline

HRID 1640131Notes

Reaction equation

HRID 1640131 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[C:11]([N+:19]([O-])=O)[CH:10]=2)[CH2:4][CH2:3]1>CCOC(C)=O.[Pd]>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:10]=[C:11]([CH:12]=[C:13]([C:15]([F:18])([F:16])[F:17])[CH:14]=2)[NH2:19])[CH2:4][CH2:3]1

Participants

4

Reactant 1

HCID 589023661-Methyl-4-[[3-nitro-5-(trifluoromethyl)phenyl]methyl]piperazine

Product 1

HCID 231550523-((4-Methylpiperazin-1-yl)methyl)-5-(trifluoromethyl)anilineYield 90.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-methyl-4-[3-nitro-5-(trifluoromethyl)benzyl]piperazine (0.35 g, 1.15 mmol) in EtOAc (15 mL) was added Pd (10% on C, 0.035 g). The reaction mixture was allowed to stir at rt under an atmosphere of hydrogen over night. The reaction mixture was filtered through Celite, washed with EtOAc, and concentrated to give 3-[(4-methylpiperazin-1-yl)methyl]-5-(trifluoromethyl)aniline (0.285 g, 90%) as a white solid which was used without further purification.

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. washwashed with EtOAc
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-51bbbf4ceb77415a99b52236a0bb0e45
Source dataset
uspto-grants-2012_02
Patent number
US08110687B2

Reaction notes

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