Ethyl Acetate → HCID 19827119, compound

HRID 1086247Notes

Reaction equation

HRID 1086247 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.[N:22]1(NC(=O)C(Br)C)[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH2:25][CH2:24][CH2:23]1.[C:38](=[O:41])([O-])[O-].[K+].[K+].[C:44](OCC)(=O)[CH3:45]>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]([CH:44]([C:38]([N:22]3[C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[CH2:25][CH2:24][CH2:23]3)=[O:41])[CH3:45])[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 19827113HCID 19827113, compound

Product 1

HCID 19827119HCID 19827119, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 300 mg of 1-[bis(4-fluorophenyl)methyl]piperazine and 280 mg of N-(1,2,3,4-tetrahydro-1-quinolyl)-2-bromopropionamide was dissolved in 20 ml of a 1:1 by volume mixture of tetrahydrofuran and N,N-dimethylformamide, and 100 mg of anhydrous potassium carbonate were added to the resulting solution. The solution was then stirred at 90° C. for 2 hours, after which ethyl acetate was added, and the organic layer was separated. The organic layer was washed three times with water, and dried over anhydrous magnesium sulfate. The solvent was then removed by evaporation under reduced pressure, and the resulting 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 give a purified 1-[bis(4-fluorophenyl)methyl]-4-[1-(1,2,3,4-tetrahydroquinoline-1-carbonyl)ethyl]piperazine.

Workup

  1. additionwere added to the resulting 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 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-5a6cd78eb09a4afbaa9b4884cb3f5cd8
Source dataset
uspto-grants-1991_07
Patent number
US05028610

Reaction notes

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