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

HRID 1042657Notes

Reaction equation

HRID 1042657 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-ff1e64aa5a564e9e8eb411984f236f97
Source dataset
uspto-grants-2013_10
Patent number
US08557996B2

Reaction notes

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