Trifluoroacetic acid → 4-(4-Cyclopropylpiperazin-1-yl)aniline

HRID 1179237Notes

Reaction equation

HRID 1179237 reaction equation
[CH:1]1([N:4]2[CH2:9][CH2:8][N:7]([C:10]3[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][CH:11]=3)[CH2:6][CH2:5]2)[CH2:3][CH2:2]1.FC(F)(F)C(O)=O.[H][H]>CO.[Pd]>[CH:1]1([N:4]2[CH2:5][CH2:6][N:7]([C:10]3[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][CH:11]=3)[CH2:8][CH2:9]2)[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 58976363HCID 58976363, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 242791844-(4-Cyclopropylpiperazin-1-yl)anilineYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 1-cyclopropyl-4-(4-nitro-phenyl)-piperazine (1.24 g, 5.00 mmol) in methanol (25 mL) was added Pd/C (10%, 100 mg) and trifluoroacetic acid (1.0 mL). The mixture was stirred under 1 atm of hydrogen (balloon) overnight, filtered and concentrated. To the residue was added water and 1N aq. NaOH to adjust the PH>11. The mixture was extracted ethyl acetate, and the organic layer was dried over Na2SO4, concentrated to give the title compound (1.08 g, 100%) as a brown oil. MS (ES+): m/z=218.1.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. additionTo the residue was added water and 1N aq. NaOH
  4. extractionThe mixture was extracted ethyl acetate
  5. dry with materialthe organic layer was dried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-35787f980f8d4395aa7f0d1eade8f4c1
Source dataset
uspto-grants-2007_10
Patent number
US07279469B2

Reaction notes

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