Water → (4-Benzylpiperazin-1-yl)-(4-trifluoromethylphenyl)amine

HRID 856059Notes

Reaction equation

HRID 856059 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][CH:3]=1.[CH2:12]([N:19]1[CH2:24][CH2:23][N:22]([NH2:25])[CH2:21][CH2:20]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.CC(C)([O-])C.[Na+].O>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1C=CC(P(C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:12]([N:19]1[CH2:20][CH2:21][N:22]([NH:25][C:2]2[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][CH:3]=2)[CH2:23][CH2:24]1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

8

Reactant 4

HCID 962WaterHCID 67872Benzene, 1-bromo-4-(trifluoromethyl)-HCID 121984534-Benzylpiperazin-1-amineHCID 23676156Sodium t-butoxide

Product 1

HCID 23081308(4-Benzylpiperazin-1-yl)-(4-trifluoromethylphenyl)amineYield 59.8%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 634876Binap, (A+-)-CatalystHCID 1140TolueneSolvent

Procedure

A mixture of 4-bromobenzotrifluoride (3.00 g, 13.3 mmol), 4-benzylpiperazin-1-yl-amine (3.06 g, 16.0 mmol), palladium acetate (60 mg, 0.267 mmol), (S)-(−)-BINAP (174 mg, 0.280 mmol) and sodium tert-butoxide (1.92 g, 20.0 mmol) in toluene (60 ml) was refluxed under a nitrogen atmosphere for 7 hours. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with brine, dried over sodium sulfate, and then filtered. The filtrate was concentrated under reduced pressure, and the residue was then purified by silica gel column chromatography (n-hexane/acetone=4/1) to afford (4-benzylpiperazin-1-yl)-(4-trifluoromethylphenyl)amine (2.666 g, yield 59%) as a pale yellow oil.

Workup

  1. temperaturewas refluxed under a nitrogen atmosphere for 7 hours
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customthe residue was then purified by silica gel column chromatography (n-hexane/acetone=4/1)

Sources & evidence

ORD record
ord-e7da10e85eaf4a6e8ae7eb290deae6b5
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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