Ethyl Acetate → HCID 10345051, compound

HRID 1086243Notes

Reaction equation

HRID 1086243 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][CH:13]([CH3:15])[NH:12][CH2:11][CH:10]2[CH3:16])=[CH:4][CH:3]=1.[CH3:24][O:25][C:26]1[CH:31]=[CH:30][C:29]([NH:32][C:33](=[O:36])[CH2:34]Cl)=[CH:28][CH:27]=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][CH:13]([CH3:15])[N:12]([CH2:34][C:33](=[O:36])[NH:32][C:29]3[CH:30]=[CH:31][C:26]([O:25][CH3:24])=[CH:27][CH:28]=3)[CH2:11][CH:10]2[CH3:16])=[CH:22][CH:21]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 311232-Chloro-N-(4-methoxyphenyl)acetamideHCID 15143636HCID 15143636, compound

Product 1

HCID 10345051HCID 10345051, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 416 mg of 1-[bis(4-fluorophenyl)methyl]-2,5-dimethylpiperazine and 316 mg of N-(4-methoxyphenyl)chloroacetamide was dissolved in 5 ml of a 1:1 by volume mixture of tetrahydrofuran and N,N-dimethylformamide. 365 mg of anhydrous potassium carbonate were then added to the solution, and the reaction mixture was stirred at 80° C. for 5 hours. At the end of this time, ethyl acetate was added to the mixture, 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, and 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 afford a purified 1-[bis(4-fluorophenyl)methyl]-4-[(4-methoxyphenyl) carbamoylmethyl]-2,5-dimethylpiperazine, melting at 131° C.

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 removed by evaporation under reduced pressure
  5. additionby volume mixture of cyclohexane and ethyl acetate as the developing solvent

Sources & evidence

ORD record
ord-8caa245f6b824f40b89ae02cb10f5ee8
Source dataset
uspto-grants-1991_07
Patent number
US05028610

Reaction notes

Loading…