Potassium Carbonate → HCID 14423672, compound

HRID 2106658Notes

Reaction equation

HRID 2106658 reaction equation
[O:1]=[C:2]([C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][CH2:18][CH2:19]Cl)=[CH:12][CH:11]=1)[CH2:3][CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[CH3:21][C:22]1[CH:23]=[C:24]([N:28]2[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]2)[CH:25]=[CH:26][CH:27]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C1(C)C=CC=CC=1>[O:1]=[C:2]([C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][CH2:18][CH2:19][N:31]2[CH2:32][CH2:33][N:28]([C:24]3[CH:25]=[CH:26][CH:27]=[C:22]([CH3:21])[CH:23]=3)[CH2:29][CH2:30]2)=[CH:12][CH:11]=1)[CH2:3][CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 831111-(m-Tolyl)piperazineHCID 14423671HCID 14423671, compound

Product 1

HCID 14423672HCID 14423672, compoundYield 58.5%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Procedure

20 g of ethyl 4-oxo-4-[4-(4-chlorobutyl)phenyl]butyrate and 12 g of 1-(3-methylphenyl)piperazine are dissolved in a mixed solvent of 80 ml of dimethylformamide and 80 ml of toluene. To this solution, 14 g of potassium carbonate is added, and this is followed by reflux with heating for 18 hours under stirring the solution. After the completion of the reaction, the reaction liquid is concentrated under reduced pressure and extracted with ethyl acetate. After being washed with water, the extract is dried over anhydrous magnesium sulfate, and the solvent is distilled off under reduced pressure. The resulting oily substance is purified by silica gel column chromatography, after which it is crystallized with isopropyl ether to give 17.2 g of ethyl 4-oxo-4-[4-(4-(4-(3-methylphenyl)piperazin-1-yl)butyl)phenyl ]butyrate having a melting point of 62° to 63° C.

Workup

  1. temperatureby reflux
  2. temperaturewith heating for 18 hours
  3. customAfter the completion of the reaction
  4. customthe reaction liquid
  5. concentrationis concentrated under reduced pressure
  6. extractionextracted with ethyl acetate
  7. washAfter being washed with water
  8. dry with materialthe extract is dried over anhydrous magnesium sulfate
  9. distillationthe solvent is distilled off under reduced pressure
  10. customThe resulting oily substance is purified by silica gel column chromatography
  11. customafter which it is crystallized with isopropyl ether

Sources & evidence

ORD record
ord-d3ef045ef1564218bf26141c7323a34a
Source dataset
uspto-grants-1990_06
Patent number
US04931443

Reaction notes

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