Ethyl Acetate → HCID 23081333, compound

HRID 856044Notes

Reaction equation

HRID 856044 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.[N:12]1([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.CC(C)([O-])C.[Na+].C(OCC)(=O)C>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.O>[F:9][C:8]([F:11])([F:10])[C:5]1[CH:6]=[CH:7][C:2]([N:15]2[CH2:14][CH2:13][N:12]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:17][CH2:16]2)=[CH:3][CH:4]=1

Participants

9

Reactant 4

HCID 8857Ethyl AcetateHCID 67872Benzene, 1-bromo-4-(trifluoromethyl)-HCID 143452tert-Butyl piperazine-1-carboxylateHCID 23676156Sodium t-butoxide

Product 1

HCID 23081333HCID 23081333, compoundYield 87%

Reagents, catalysts & solvents 4

HCID 80271Tri-o-tolylphosphineCatalystHCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A mixture of 4-bromobenzotrifluoride (3.0 g, 13.3 mmol), tert-butyl piperazine-1-carboxylate (2.9 g, 15.3 mmol), bis(dibenzylideneacetone)palladium (306 mg, 0.53 mmol), tri-o-tolylphosphine (162 mg, 0.53 mmol), and sodium tert-butoxide (2.2 g, 22.7 mmol) in toluene (60 ml) was refluxed under a nitrogen atmosphere for 4 hours. Ethyl acetate and water were added to the reaction mixture, which was stirred for a while, and the insoluble substances were removed by filtration through Celite, and the filtrate was then extracted with ethyl acetate. The extract was washed with brine, dried over magnesium sulfate, and then filtered. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexane/methylene chloride=2/1) to afford tert-butyl 4-(4-trifluoromethylphenyl)-piperazine-1-carboxylate (3.8 g, yield 87%) as a white powder.

Workup

  1. temperaturewas refluxed under a nitrogen atmosphere for 4 hours
  2. customthe insoluble substances were removed by filtration through Celite
  3. extractionthe filtrate was then extracted with ethyl acetate
  4. washThe extract was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (n-hexane/methylene chloride=2/1)

Sources & evidence

ORD record
ord-a993bccab943457f9845bd8d65c64de7
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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