Potassium Carbonate → Ethyl 4-(4-cyclobutylpiperazin-1-yl)benzoate

HRID 1911395Notes

Reaction equation

HRID 1911395 reaction equation
F[C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.[CH:13]1([N:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)[CH2:16][CH2:15][CH2:14]1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[CH:13]1([N:17]2[CH2:22][CH2:21][N:20]([C:2]3[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=3)[CH2:19][CH2:18]2)[CH2:16][CH2:15][CH2:14]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 67976Benzoic acid, 4-fluoro-, ethyl esterHCID 47386021-Cyclobutylpiperazine

Product 1

HCID 57440408Ethyl 4-(4-cyclobutylpiperazin-1-yl)benzoateYield 33%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

Ethyl 4-fluorobenzoate (0.753 g, 4.48 mmol) was added to a solution of 1-cyclobutylpiperazine (0.571 g, 4.07 mmol) and potassium carbonate (0.563 g, 4.07 mmol) in DMSO (8 mL) under nitrogen. The resulting solution was stirred at 100° C. for 18 h and evaporated to dryness. The residue was triturated with diethyl ether, filtered, and evaporated and the crude product was purified by silica column chromatography, eluting with a gradient of 0 to 2.5% 2.5N MeOH in DCM. Pure fractions were evaporated to dryness to afford ethyl 4-(4-cyclobutylpiperazin-1-yl)benzoate (0.387 g, 32.9%) as a white solid.

Workup

  1. customevaporated to dryness
  2. customThe residue was triturated with diethyl ether
  3. filtrationfiltered
  4. customevaporated
  5. customthe crude product was purified by silica column chromatography
  6. washeluting with a gradient of 0 to 2.5% 2.5N MeOH in DCM
  7. customPure fractions were evaporated to dryness

Sources & evidence

ORD record
ord-b1002a32f0794f81a9f3cdc3a244c73f
Source dataset
uspto-grants-2013_12
Patent number
US08604022B2

Reaction notes

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