3-Chloroaniline → 6-{1-Oxo-2-[4-(3-chlorophenyl)-1-piperazinyl]-ethyl}-3,4-dihydrocarbostyril

HRID 1263129Notes

Reaction equation

HRID 1263129 reaction equation
Cl.[O:2]=[C:3]([C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[NH:17][C:16](=[O:21])[CH2:15][CH2:14]2)[CH2:4][N:5]1[CH2:10][CH2:9]O[CH2:7][CH2:6]1.[Cl:22][C:23]1[CH:24]=[C:25]([CH:27]=[CH:28][CH:29]=1)[NH2:26]>Cl>[O:2]=[C:3]([C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[NH:17][C:16](=[O:21])[CH2:15][CH2:14]2)[CH2:4][N:5]1[CH2:10][CH2:9][N:26]([C:25]2[CH:27]=[CH:28][CH:29]=[C:23]([Cl:22])[CH:24]=2)[CH2:7][CH2:6]1

Participants

4

Reactant 2

HCID 79323-ChloroanilineHCID 202294546-(1-Oxo-2-morpholinoethyl)-3,4-dihydrocarbostyril monohydrochloride

Product 1

HCID 130648586-{1-Oxo-2-[4-(3-chlorophenyl)-1-piperazinyl]-ethyl}-3,4-dihydrocarbostyril

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

5.0 Grams of 6-(1-oxo-2-morpholinoethyl)-3,4-dihydrocarbostyril monohydrochloride and 5.0 g of m-chloroaniline were mixed in 30 ml of concentrated hydrochloric acid and the mixture was heated at 200°-220° C. by removing water for 6 hours. After cooled the reaction mixture 100 ml of 5N-hydrochloric acid was added thereto and dissolved by heating and refluxed for 2 hours. Then the reaction mixture was cooled and poured into 100 ml of 8N-sodium hydroxide aqueous solution and the organic layer was extracted with chloroform. Chloroform was removed by distillation and the residue thus obtained was separated and purified by a preparative silica-gel thin layer chromatography, then recrystallized from dioxane-water to obtain 0.16 g of 6-{1-oxo-2-[4-(3-chlorophenyl)-1-piperazinyl]-ethyl}-3,4-dihydrocarbostyril in light yellow needle-like crystals.

Workup

  1. temperaturethe mixture was heated at 200°-220° C.
  2. customby removing water for 6 hours
  3. temperatureAfter cooled the reaction mixture 100 ml of 5N-hydrochloric acid
  4. additionwas added
  5. dissolutiondissolved
  6. temperatureby heating
  7. temperaturerefluxed for 2 hours
  8. temperatureThen the reaction mixture was cooled
  9. additionpoured into 100 ml of 8N-sodium hydroxide aqueous solution
  10. extractionthe organic layer was extracted with chloroform
  11. customChloroform was removed by distillation
  12. customthe residue thus obtained
  13. customwas separated
  14. custompurified by a preparative silica-gel thin layer chromatography
  15. customrecrystallized from dioxane-water

Sources & evidence

ORD record
ord-e950b3adc1d64702975384c6c4d6880f
Source dataset
uspto-grants-1984_06
Patent number
US04455422

Reaction notes

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