Ethyl Acetate → 1-[Bis(4-fluorophenyl)methyl]-4-[(2,4,6-trimethylphenyl)carbamoylmethyl]-3-methylpiperazine

HRID 1086242Notes

Reaction equation

HRID 1086242 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[N:9]2[CH2:14][CH2:13][NH:12][CH:11]([CH3:15])[CH2:10]2)=[CH:4][CH:3]=1.[CH3:23][C:24]1[CH:29]=[C:28]([CH3:30])[CH:27]=[C:26]([CH3:31])[C:25]=1[NH:32][C:33](=[O:36])[CH2:34]Cl.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>O1CCCC1.CN(C)C=O>[F:22][C:19]1[CH:18]=[CH:17][C:16]([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]([CH2:34][C:33](=[O:36])[NH:32][C:25]3[C:24]([CH3:23])=[CH:29][C:28]([CH3:30])=[CH:27][C:26]=3[CH3:31])[CH:11]([CH3:15])[CH2:10]2)=[CH:21][CH:20]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 23056352-chloro-N-(2,4,6-trimethylphenyl)acetamideHCID 214599471-[Bis(4-fluorophenyl)methyl]-3-methylpiperazine

Product 1

HCID 198271221-[Bis(4-fluorophenyl)methyl]-4-[(2,4,6-trimethylphenyl)carbamoylmethyl]-3-methylpiperazine

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 300 mg of 1-[bis(4-fluorophenyl)methyl]-3-methylpiperazine and 252 mg of N-(2,4,6-trimethylphenyl) chloroacetamide was dissolved in 20 ml of a 1:1 by volume mixture of tetrahydrofuran and N,N-dimethylformamide. 100 mg of anhydrous potassium carbonate were then added to the solution, and the reaction mixture was stirred at 70° C. for 3 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 then removed by evaporation under reduced pressure, and the residue was subjected to silica gel thin layer chromatography using a 1:1 by volume mixture of cyclohexane and ethyl acetate as the developing solvent, to afford a purified 1-[bis(4-fluorophenyl)methyl]-4-[(2,4,6-trimethylphenyl)carbamoylmethyl]-3-methylpiperazine.

Workup

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

Sources & evidence

ORD record
ord-9042eb4943b2425f99725d4f8a51a7b2
Source dataset
uspto-grants-1991_07
Patent number
US05028610

Reaction notes

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