Trifluoroacetic acid → Piperazin-1-yl-(4-trifluoromethylbenzylidene)-amine

HRID 856057Notes

Reaction equation

HRID 856057 reaction equation
[N:1]1([NH:7][C:8](=O)OC(C)(C)C)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.FC(F)(F)C(O)=O.[F:22][C:23]([F:33])([F:32])[C:24]1[CH:31]=[CH:30][C:27](C=O)=[CH:26][CH:25]=1.C(=O)([O-])O.[Na+]>C(Cl)Cl>[N:1]1([N:7]=[CH:8][C:27]2[CH:30]=[CH:31][C:24]([C:23]([F:33])([F:32])[F:22])=[CH:25][CH:26]=2)[CH2:2][CH2:3][NH:4][CH2:5][CH2:6]1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 679964-(Trifluoromethyl)benzaldehydeHCID 516892Sodium BicarbonateHCID 21701658tert-Butyl piperazin-1-ylcarbamate

Product 1

HCID 69481693Piperazin-1-yl-(4-trifluoromethylbenzylidene)-amineYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Tert-butyl piperazin-1-yl-carbamate (403 mg, 2.0 mmol) was suspended in methylene chloride (4 ml), to which trifluoroacetic acid (1.6 ml) was added, and the mixture was stirred at room temperature for 5 minutes. To which 4-(trifluoromethyl)benzaldehyde (0.3 ml, 2.2 mmol) was added, and the resulting mixture was stirred at room temperature for 1 hour. The reaction mixture was poured into sodium hydrogencarbonate aqueous solution, and extracted with ethyl acetate. The extract was washed with brine, dried over sodium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (methylene chloride/methanol=9/1) to afford piperazin-1-yl-(4-trifluoromethylbenzylidene)-amine (432 mg, yield 84%) as a colorless crystalline powder.

Workup

  1. additionwas added
  2. stirringthe resulting mixture was stirred at room temperature for 1 hour
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (methylene chloride/methanol=9/1)

Sources & evidence

ORD record
ord-272d294f2939499a9aeaecbe437c43a3
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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