Hydrochloric Acid → HCID 70436070, compound

HRID 255660Notes

Reaction equation

HRID 255660 reaction equation
[C:1]1([CH:7]=[CH:8][C:9](=[O:15])[CH2:10][C:11]([O:13]C)=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([N:19]1[CH2:24][CH2:23][N:22]([C:25]2[CH:31]=[CH:30][C:28]([NH2:29])=[CH:27][CH:26]=2)[CH2:21][CH2:20]1)(=O)C.[Cl:32][C:33]1C(=O)C(Cl)=C(Cl)C(=O)C=1Cl.[ClH:44]>C1C=CC=CC=1.CN(C)C=O.O1CCOCC1>[ClH:32].[ClH:44].[C:1]1([C:7]2[N:29]([C:28]3[CH:30]=[CH:31][C:25]([N:22]4[CH2:23][CH2:24][NH:19][CH2:20][CH2:21]4)=[CH:26][CH:27]=3)[CH:33]=[C:10]([C:9](=[O:15])[CH:8]=2)[C:11]([OH:13])=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 8371ChloranilHCID 7362691-[4-(4-Aminophenyl)piperazin-1-yl]ethan-1-oneHCID 53792279HCID 53792279, compound

Product 1

HCID 70436070HCID 70436070, compound

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 6228DimethylformamideSolventHCID 312751,4-DioxaneSolvent

Procedure

In 5 ml of benzene was dissolved 0.3 g of methyl 5-phenyl-3-oxo-4-pentenoate, and 0.2 g of N,N-dimethylformamidodimethylacetal was added to the solution. They were reacted at 60°-70° C. for 2 hours. The reaction mixture was cooled to room temperature, and 0.3 g of 4-(4-acetylpiperazino)-aniline was added thereto. The mixture was subjected to reaction at room temperature for 4 hours. After completion of the reaction, the solvent was removed by distillation under reduced pressure, and the oily substance thus obtained was dissolved in 5 ml of N,N-dimethylformamide, and they were refluxed for 5 hours. After completion of the reaction, the solvent was removed by distillation under reduced pressure, and the residue was purified by a column chromatography (Wako Silica Gel C-200; eluent: chloroform/ethanol (25:1 by volume) mixture). The fraction containing the objective substance was concentrated, and the oily substance thus obtained was dissolved in 4 ml of dioxane, and 0.12 g of 2,3,5,6-tetrachloro-p-benzoquinone was added thereto. They were reacted at 90°-100° C. for 30 minutes. After completion of the reaction, the solvent was removed by distillation under reduced pressure, and the residue was purified by a column chromatography (Wako Silica Gel C-200; eluent: chloroform/ethanol (100:3 by volume) mixture). The fraction containing the objective substance was concentrated, and to the crystals thus formed were added 3 ml of 6N hydrochloric acid, and the resulting mixture was refluxed for 2 hours. Water was removed by distillation under reduced pressure, to obtain 0.12 g of 6-phenyl-1-(4 -piperazinophenyl)-4-oxo-1,4-dihydronicotinic acid dihydrochloride having a melting point of 211°-213° C. (decomp.)

Workup

  1. additionwas added to the solution
  2. customThey were reacted at 60°-70° C. for 2 hours
  3. customThe mixture was subjected to reaction at room temperature for 4 hours
  4. customAfter completion of the reaction
  5. customthe solvent was removed by distillation under reduced pressure
  6. customthe oily substance thus obtained
  7. temperaturethey were refluxed for 5 hours
  8. customAfter completion of the reaction
  9. customthe solvent was removed by distillation under reduced pressure
  10. customthe residue was purified by a column chromatography (Wako Silica Gel C-200; eluent: chloroform/ethanol (25:1 by volume) mixture)
  11. additionThe fraction containing the objective substance
  12. concentrationwas concentrated
  13. customthe oily substance thus obtained
  14. customThey were reacted at 90°-100° C. for 30 minutes
  15. customAfter completion of the reaction
  16. customthe solvent was removed by distillation under reduced pressure
  17. customthe residue was purified by a column chromatography (Wako Silica Gel C-200; eluent: chloroform/ethanol (100:3 by volume) mixture)
  18. additionThe fraction containing the objective substance
  19. concentrationwas concentrated
  20. customto the crystals thus formed
  21. temperaturethe resulting mixture was refluxed for 2 hours
  22. customWater was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-f3cc779a7d114dfe9ae80f6d53603a28
Source dataset
uspto-grants-1987_10
Patent number
US04698352

Reaction notes

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