Methyl Isobutyl Ketone → (E)-ethyl 4-[methyl(3-phenyl-2-propenyl)amino]-1-piperidinecarboxylate ethanedioate

HRID 466533

Reaktionsgleichung

Reaktionsgleichung von HRID 466533
[CH3:1][NH:2][CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:5][CH2:4]1.Cl[CH2:15][CH:16]=[CH:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[C:24](=[O:27])([O-:26])[O-].[Na+].[Na+].CC(C)CC(=O)C>O>[C:9]([OH:11])(=[O:10])[C:24]([OH:26])=[O:27].[CH3:1][N:2]([CH2:15]/[CH:16]=[CH:17]/[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:5][CH2:4]1

Komponenten

6

Edukt 4

HCID 7909Methyl Isobutyl KetoneHCID 10340Sodium CarbonateHCID 94242Benzene, (3-chloro-1-propenyl)-HCID 110631401-Piperidinecarboxylic acid, 4-(methylamino)-, ethyl ester

Produkt 1

HCID 86744664(E)-ethyl 4-[methyl(3-phenyl-2-propenyl)amino]-1-piperidinecarboxylate ethanedioate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Versuchsvorschrift

A mixture of 14 parts of ethyl 4-(methylamino)-1-piperidinecarboxylate, 13 parts of (3-chloro-1-propenyl)benzene, 26.5 parts of sodium carbonate and 240 parts of 4-methyl-2-pentanone was stirred and refluxed over week-end using a water separator. The reaction mixture was cooled, water was added and the layers were separated. The organic phase was dried, filtered and evaporated. The residue was converted into the ethanedioate salt in 2-propanol and 2-propanone. The salt was filtered off and dried, yielding 23.4 parts of (E)-ethyl 4-[methyl(3-phenyl-2-propenyl)amino]-1-piperidinecarboxylate ethanedioate (1:1); mp. 160.2° C. (intermediate 3).

Aufarbeitung

  1. temperaturerefluxed over week-end
  2. temperatureThe reaction mixture was cooled
  3. customthe layers were separated
  4. customThe organic phase was dried
  5. filtrationfiltered
  6. customevaporated
  7. filtrationThe salt was filtered off
  8. customdried

Quellen und Nachweise

ORD-Eintrag
ord-6a171b240b114221a4d4a08d730c2daf
Quelldatensatz
uspto-grants-1992_10
Patentnummer
US05157035

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