Ethyl Acetate → HCID 10347573, compound

HRID 496034Notes

Reaction equation

HRID 496034 reaction equation
Br[CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[C:7]([O:13][CH3:14])[CH:6]=1.[F:15][C:16]1[CH:21]=[CH:20][C:19]([CH:22]([C:35]2[CH:40]=[CH:39][C:38]([F:41])=[CH:37][CH:36]=2)[CH2:23][CH2:24][CH2:25][CH2:26][C:27]([N:29]2[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]2)=[O:28])=[CH:18][CH:17]=1.C([O-])([O-])=O.[K+].[K+].CCOC(C)=O>CN(C=O)C>[CH3:14][O:13][C:7]1[CH:6]=[C:5]([CH:10]=[CH:9][C:8]=1[O:11][CH3:12])[O:4][CH2:3][CH2:2][N:32]1[CH2:33][CH2:34][N:29]([C:27](=[O:28])[CH2:26][CH2:25][CH2:24][CH2:23][CH:22]([C:19]2[CH:18]=[CH:17][C:16]([F:15])=[CH:21][CH:20]=2)[C:35]2[CH:40]=[CH:39][C:38]([F:41])=[CH:37][CH:36]=2)[CH2:30][CH2:31]1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 22324249HCID 22324249, compoundHCID 22324251HCID 22324251, compound

Product 1

HCID 10347573HCID 10347573, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 4-(2-bromo-ethoxy)-1,2-dimethoxy benzene (1.41 g, 4.86 mmol) and 6,6-bis-(4-fluorophenyl)-1-piperazin-1-yl-hexan-1-one (1.81 g, 4.86 mmol.) in dry DMF (40 ml) was added K2CO3 (0.8 g, 5.83 mmol.) and the mixture stirred at 120° C. overnight. EtOAc was added, washed with water (2×30 ml), brine (3×10 ml), dried over MgSO4, and evaporated under reduced pressure. The produce was purified by column chromatography on silica (hexane:EtOAc 1:1), followed by EtOAc to give the desired product in 57% yield.

Workup

  1. washwashed with water (2×30 ml), brine (3×10 ml)
  2. dry with materialdried over MgSO4
  3. customevaporated under reduced pressure
  4. customThe produce was purified by column chromatography on silica (hexane:EtOAc 1:1)

Sources & evidence

ORD record
ord-c59ac600d94641c69a6409c09b397e82
Source dataset
uspto-grants-2005_09
Patent number
US06943168B2

Reaction notes

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