Hydrochloric Acid → 2,4'-Dimethyl-3-(4-isobutylpiperazino)propiophenone dihydrochloride

HRID 1277382

Reaktionsgleichung

Reaktionsgleichung von HRID 1277382
[ClH:1].[CH3:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:12])[CH2:10][CH3:11])=[CH:5][CH:4]=1.Cl.Cl.[CH2:15]([N:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1)[CH:16]([CH3:18])[CH3:17].O1CC[CH2:28]OO1>CCOCC.C(O)C.C1(C)C=CC=CC=1.[N+](C)([O-])=O>[ClH:1].[ClH:1].[CH3:11][CH:10]([CH2:28][N:22]1[CH2:23][CH2:24][N:19]([CH2:15][CH:16]([CH3:18])[CH3:17])[CH2:20][CH2:21]1)[C:9]([C:6]1[CH:7]=[CH:8][C:3]([CH3:2])=[CH:4][CH:5]=1)=[O:12]

Komponenten

9

Edukt 4

HCID 313Hydrochloric AcidHCID 21429p-MethylpropiophenoneHCID 27593881-Isobutylpiperazine dihydrochlorideHCID 19593658CID 19593658

Produkt 1

HCID 129522882,4'-Dimethyl-3-(4-isobutylpiperazino)propiophenone dihydrochlorideAusbeute 46,5 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 702EthanolLösungsmittelHCID 1140TolueneLösungsmittelHCID 3283Diethyl EtherLösungsmittelHCID 6375NitromethaneLösungsmittel

Versuchsvorschrift

A mixture of 125 ml of nitromethane, 35 ml of toluene, 20 ml of ethanol, and 1 ml of concentrated hydrochloric acid was mixed together with 18.6 g of 4'-methylpropiophenone, 27.0 g of N-isobutylpiperazine dihydrochloride and 8.5 g of trioxane. The mixture was heated with stirring under reflux for 4 hrs. while distilling off water generated through the reaction. After cooling, the reaction mixture was added with ether, and the precipitate was filtered, which was dissolved in water. The solution was adjusted to pH 6 with 5 N sodium hydroxide, washed with ether, and furtheradjusted to pH 7 with 5 N sodium hydroxide. The obtained solution was extracted with ether and the extract was dried, and white crystals generated by introducing dry hydrogen chloride were filtered and dried. The product was recrystallized from an ethanol-acetone mixed solvent, yielding 2,4'-dimethyl-3-(4-isobutylpiperazino)propiophenone dihydrochloride. (yield 46.5%), m.p. 215°-220° C.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 4 hrs
  3. distillationwhile distilling off water
  4. customgenerated through the reaction
  5. temperatureAfter cooling
  6. filtrationthe precipitate was filtered
  7. dissolutionwhich was dissolved in water
  8. washwashed with ether
  9. extractionThe obtained solution was extracted with ether
  10. customthe extract was dried
  11. additionby introducing dry hydrogen chloride
  12. filtrationwere filtered
  13. customdried
  14. customThe product was recrystallized from an ethanol-acetone mixed solvent

Quellen und Nachweise

ORD-Eintrag
ord-a6eda1ab6379447c911069877d2a001a
Quelldatensatz
uspto-grants-1981_07
Patentnummer
US04277474

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