Ethyl Acetate → 1-[Bis(4-fluorophenyl)methyl]-4-[(3-fluorophenyl)carbamoylmethyl]-3,3-dimethylpiperazine

HRID 1086248Notes

Reaction equation

HRID 1086248 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)[N:9]2[CH2:14][CH2:13][NH:12][C:11]([CH3:16])([CH3:15])[CH2:10]2)=[CH:4][CH:3]=1.[F:24][C:25]1[CH:26]=[C:27]([NH:31][C:32](=[O:35])[CH2:33]Cl)[CH:28]=[CH:29][CH:30]=1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>O1CCCC1.CN(C)C=O>[F:23][C:20]1[CH:19]=[CH:18][C:17]([CH:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[N:9]2[CH2:14][CH2:13][N:12]([CH2:33][C:32](=[O:35])[NH:31][C:27]3[CH:28]=[CH:29][CH:30]=[C:25]([F:24])[CH:26]=3)[C:11]([CH3:16])([CH3:15])[CH2:10]2)=[CH:22][CH:21]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 23889312-chloro-N-(3-fluorophenyl)acetamideHCID 198271101-[Bis(4-fluorophenyl)methyl]-3,3-dimethylpiperazine

Product 1

HCID 198271141-[Bis(4-fluorophenyl)methyl]-4-[(3-fluorophenyl)carbamoylmethyl]-3,3-dimethylpiperazine

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 283 mg of 1-[bis(4-fluorophenyl)methyl]-3,3-dimethylpiperazine and 204 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 1 g of anhydrous potassium carbonate was added to the resulting solution. The reaction mixture was then stirred at 80° C. for 16 hours, after which ethyl acetate was added, and the organic layer was separated. The organic layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was then 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-fluorophenyl)carbamoylmethyl]-3,3-dimethylpiperazine.

Workup

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

Sources & evidence

ORD record
ord-cd7b3d00e56b49f39b9a8463405857fa
Source dataset
uspto-grants-1991_07
Patent number
US05028610

Reaction notes

Loading…