Potassium Carbonate → HCID 4742802, compound

HRID 1645803Notes

Reaction equation

HRID 1645803 reaction equation
C(=O)([O-])[O-].[K+].[K+].[OH:7][CH2:8][CH2:9][N:10]1[CH2:15][CH2:14][N:13]([CH2:16][CH:17]=[CH:18][C:19]2[O:20][CH:21]=[CH:22][CH:23]=2)[CH2:12][CH2:11]1.[F:24][C:25]1[CH:30]=[CH:29][C:28]([CH:31](Cl)[C:32]2[S:33][CH:34]=[CH:35][CH:36]=2)=[CH:27][CH:26]=1>C1(C)C=CC=CC=1>[F:24][C:25]1[CH:26]=[CH:27][C:28]([CH:31]([C:32]2[S:33][CH:34]=[CH:35][CH:36]=2)[O:7][CH2:8][CH2:9][N:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH:17]=[CH:18][C:19]3[O:20][CH:21]=[CH:22][CH:23]=3)[CH2:12][CH2:11]2)=[CH:29][CH:30]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 19802549HCID 19802549, compoundHCID 54373614HCID 54373614, compound

Product 1

HCID 4742802HCID 4742802, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

1.16 g (0.0084 mol) potassium carbonate were added to a solution of 1.00 g (0.0042 mol) 1-(2-hydroxyethyl)-4-[3-(2-furyl)-2-propenyl]piperazine and 1.16 g (0.0084 mol) (4-fluorophenyl)(2-thienyl)methylchloride in 50 ml toluene. The mixture was refluxed for 16 h, then cooled, diluted with 50 ml toluene and washed twice with water. The crude product obtained by evaporation in vacuo was chromatographed on silicagel (elution with dichloromethane/methanol/acetic acid 95/5/3). The combined pure fractions were adjusted to pH 12 by addition of 2N sodium hydroxide solution, subsequently washed with water and brine and concentrated in vacuo. The oily residue was redissolved in acetonitrile and precipitated by addition of an excess of a solution of maleic acid in acetonitrile. 0.340 g (12% of the theoretical yield) of the title compound were obtained as the dimaleate salt, m.p. 169°-71° C.

Workup

  1. temperatureThe mixture was refluxed for 16 h
  2. temperaturecooled
  3. washwashed twice with water
  4. customThe crude product obtained by evaporation in vacuo
  5. customwas chromatographed on silicagel (elution with dichloromethane/methanol/acetic acid 95/5/3)
  6. additionThe combined pure fractions were adjusted to pH 12 by addition of 2N sodium hydroxide solution
  7. washsubsequently washed with water and brine
  8. concentrationconcentrated in vacuo
  9. dissolutionThe oily residue was redissolved in acetonitrile
  10. customprecipitated by addition of an excess of a solution of maleic acid in acetonitrile

Sources & evidence

ORD record
ord-01cddf8812724dc1bcc3515f46a5840c
Source dataset
uspto-grants-1993_01
Patent number
US05177077

Reaction notes

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