Potassium Carbonate → ethyl 5-[4-[3-[9-(2,2,2-trifluoroethylcarbamoyl)-9H-fluoren-9-yl]propyl]piperazinyl]-2-methylbenzoate

HRID 1796784Notes

Reaction equation

HRID 1796784 reaction equation
[CH3:1][C:2]1[CH:12]=[CH:11][C:10]([N:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].C(=O)([O-])[O-].[K+].[K+].[F:25][C:26]([F:49])([F:48])[CH2:27][NH:28][C:29]([C:31]1([CH2:44][CH2:45][CH2:46]Br)[C:43]2[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=2[C:37]2[C:32]1=[CH:33][CH:34]=[CH:35][CH:36]=2)=[O:30]>CN(C=O)C.C(OCC)(=O)C>[F:25][C:26]([F:48])([F:49])[CH2:27][NH:28][C:29]([C:31]1([CH2:44][CH2:45][CH2:46][N:16]2[CH2:15][CH2:14][N:13]([C:10]3[CH:11]=[CH:12][C:2]([CH3:1])=[C:3]([CH:9]=3)[C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH2:18][CH2:17]2)[C:43]2[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=2[C:37]2[C:32]1=[CH:33][CH:34]=[CH:35][CH:36]=2)=[O:30]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 105977593-[9-(2,2,2-Trifluoroethylcarbamoyl)-9H-fluoren-9-yl]propyl bromideHCID 69591845Ethyl 2-methyl-5-piperazinylbenzoate

Product 1

HCID 22180176ethyl 5-[4-[3-[9-(2,2,2-trifluoroethylcarbamoyl)-9H-fluoren-9-yl]propyl]piperazinyl]-2-methylbenzoateYield 59.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
75 °C

Procedure

Ethyl 2-methyl-5-piperazinylbenzoate (1.8 g, 9.1 mmol) was dissolved in 20 ml of anhydrous DMF. Potassium carbonate (1.7 g) and 3-[9-(2,2,2-trifluoroethylcarbamoyl)-9H-fluoren-9-yl]propyl bromide (2.5 g, 6.1 mmol) were added to the solution, and the mixture was stirred at 75° C. for 7 hr. The temperature of the reaction solution was returned to room temperature, and the reaction solution was then diluted with ethyl acetate. The dilution was washed twice with water and was then dried over anhydrous magnesium sulfate. The solvent was removed by distillation under the reduced pressure. The residue was purified by column chromatography (development system, n-hexane:ethyl acetate=2:1) to give 2.1 g (yield 59%) of ethyl 5-[4-[3-[9-(2,2,2-trifluoroethylcarbamoyl)-9H-fluoren-9-yl]propyl]piperazinyl]-2-methylbenzoate as a pale yellow foam.

Workup

  1. customwas returned to room temperature
  2. washThe dilution was washed twice with water
  3. dry with materialwas then dried over anhydrous magnesium sulfate
  4. customThe solvent was removed by distillation under the reduced pressure
  5. customThe residue was purified by column chromatography (development system, n-hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-99d843331a1d42cf9c242084d7500704
Source dataset
uspto-grants-2006_04
Patent number
US07030120B2

Reaction notes

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