Ethanol → 3-(4-Methylpiperazin-1-YL)-5-(trifluoromethyl)aniline

HRID 502702Notes

Reaction equation

HRID 502702 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:11]=[C:10]([N+:18]([O-])=O)[CH:9]=2)[CH2:4][CH2:3]1.C(O)C.[H][H]>[Pd].C(O)(=O)C>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:8]2[CH:9]=[C:10]([NH2:18])[CH:11]=[C:12]([C:14]([F:17])([F:15])[F:16])[CH:13]=2)[CH2:6][CH2:7]1

Participants

6

Reactant 3

HCID 702EthanolHCID 594280371-Methyl-4-(3-nitro-5-(trifluoromethyl)phenyl)piperazineHCID 178418361HCID 178418361, compound

Product 1

HCID 185430443-(4-Methylpiperazin-1-YL)-5-(trifluoromethyl)aniline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

Into a 100 mL round bottom flask under inert atmosphere was placed 1-methyl-4-(3-nitro-5-(trifluoromethyl)phenyl)piperazine (0.736 g, 2.54 mmol), 10% palladium on carbon (90 mg), ethanol (40 mL), and acetic acid (20 mL). The atmosphere was exchanged with hydrogen gas via balloon. The reaction was allowed to stir 3 days at room temperature, then filtered through celite and concentrated under reduced pressure to afford the crude as an orange oil. The crude mixture was purified via silica column chromatography with a solvent solution of 90%/10%/1% ratio of CH2Cl2/CH3OH/NH4OH, to afford the title compound. MS m/z=260 [M+H]+; Calc'd for C12H16F3N3: 259.3.

Workup

  1. customInto a 100 mL round bottom flask under inert atmosphere was placed
  2. filtrationfiltered through celite and
  3. concentrationconcentrated under reduced pressure
  4. customto afford the crude as an orange oil
  5. customThe crude mixture was purified via silica column chromatography with a solvent solution of 90%/10%/1% ratio of CH2Cl2/CH3OH/NH4OH

Sources & evidence

ORD record
ord-b4469069e916422bb2a0402d6999eef0
Source dataset
uspto-grants-2010_08
Patent number
US07776869B2

Reaction notes

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