Ethyl Acetate → HCID 70087477, compound

HRID 1086245Notes

Reaction equation

HRID 1086245 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[CH2:15][CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[CH:4][CH:3]=1.[C:23]12([NH:33][C:34](=[O:38])[CH:35](Br)[CH3:36])[CH2:32][CH:27]3[CH2:28][CH:29]([CH2:31][CH:25]([CH2:26]3)[CH2:24]1)[CH2:30]2.[C:39](=O)([O-:41])[O-:40].[K+].[K+].C(OCC)(=[O:47])C>O1CCCC1.CN(C)C=O>[C:34]([OH:38])(=[O:47])/[CH:35]=[CH:36]\[C:39]([OH:41])=[O:40].[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[CH2:15][CH2:14][CH2:13][N:12]([CH:35]([C:34](=[O:38])[NH:33][C:23]34[CH2:32][CH:27]5[CH2:28][CH:29]([CH2:31][CH:25]([CH2:26]5)[CH2:24]3)[CH2:30]4)[CH3:36])[CH2:11][CH2:10]2)=[CH:21][CH:20]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 5183025HCID 5183025, compoundHCID 22367730HCID 22367730, compound

Product 1

HCID 70087477HCID 70087477, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 300 mg of 1-[bis(4-fluorophenyl) methyl]homopiperazine and 300 mg of N-(1-adamantyl) -2-bromopropionamide Was dissolved in 20 ml of a 1:1 by volume mixture of tetrahydrofuran and N,N-dimethylformamide, and then 100 mg of anhydrous potassium carbonate were added to the resulting solution. The reaction mixture was stirred at 90° C. for hours, and then ethyl acetate was added, 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 1:1 by volume mixture of cyclo hexane and ethyl acetate as the developing solvent, to give a purified 1-[bis(4-fluorophenyl)methyl]-4-[1-(1-adamantylcarbamoyl)ethyl]homopiperazine.

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 cyclo hexane and ethyl acetate as the developing solvent

Sources & evidence

ORD record
ord-6cc850405e3d48db811e233c390c9c42
Source dataset
uspto-grants-1991_07
Patent number
US05028610

Reaction notes

Loading…