Ethyl Acetate → 1-[Bis(4-fluorophenyl)methyl]-4-(3-fluorophenylcarbamoylmethyl)piperazine

HRID 1086244Notes

Reaction equation

HRID 1086244 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[N:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[CH:4][CH:3]=1.[F:22][C:23]1[CH:24]=[C:25]([NH:29][C:30](=[O:33])[CH2:31]Cl)[CH:26]=[CH:27][CH:28]=1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>O1CCCC1.CN(C)C=O>[F:21][C:18]1[CH:19]=[CH:20][C:15]([CH:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[N:9]2[CH2:10][CH2:11][N:12]([CH2:31][C:30](=[O:33])[NH:29][C:25]3[CH:26]=[CH:27][CH:28]=[C:23]([F:22])[CH:24]=3)[CH2:13][CH2:14]2)=[CH:16][CH:17]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 1529321-(Bis(4-fluorophenyl)methyl)piperazineHCID 23889312-chloro-N-(3-fluorophenyl)acetamide

Product 1

HCID 151436391-[Bis(4-fluorophenyl)methyl]-4-(3-fluorophenylcarbamoylmethyl)piperazine

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 300 mg of 1-[bis(4-fluorophenyl)methyl]piperazine and 234 mg of N-(3-fluorophenyl)chloroacetamide was dissolved in 20 ml of a 1:1 by volume mixture of tetrahydrofuran and N,N-dimethylformamide, and 400 mg of anhydrous potassium carbonate were added to the solution. The reaction mixture was then stirred at 70° C. for 2 hours, after which ethyl acetate was added to it and the organic layer was separated. The organic layer was washed three times with water, and then dried over anhydrous magnesium sulfate. The solvent was removed by evaporation under reduced pressure. The residue was subjected to silica gel thin layer chromatography using a 2:1 by volume mixture of cyclohexane and ethyl acetate as the developing solvent, to give a purified 1-[bis(4-fluorophenyl)methyl]-4-(3-fluorophenylcarbamoylmethyl)piperazine.

Workup

  1. additionwere added to the solution
  2. customthe organic layer was separated
  3. washThe organic layer was washed three times with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was removed by evaporation under reduced pressure
  6. additionby volume mixture of cyclohexane and ethyl acetate as the developing solvent

Sources & evidence

ORD record
ord-454b3d32b4264765961d03b4d51848f4
Source dataset
uspto-grants-1991_07
Patent number
US05028610

Reaction notes

Loading…