Hydrochloric Acid → (+)-cis-3-methoxy-N-(1-phenylethyl)-4-piperidinamine

HRID 846778Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 846778
[CH3:1][O:2][C@H:3]1[C@@H:8]([NH:9][CH:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH3:11])[CH2:7][CH2:6][N:5](C(OCC)=O)[CH2:4]1.Cl>>[CH3:1][O:2][C@H:3]1[C@@H:8]([NH:9][CH:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH3:11])[CH2:7][CH2:6][NH:5][CH2:4]1

Komponenten

3

Edukt 2

HCID 313Hydrochloric AcidHCID 67914576(+)-Ethyl cis-3-methoxy-4-[(1-phenylethyl)amino]-1-piperidinecarboxylate

Produkt 1

HCID 67914506(+)-cis-3-methoxy-N-(1-phenylethyl)-4-piperidinamineAusbeute 100 %

Versuchsvorschrift

A solution of 16 parts of (+)-ethyl cis-3-methoxy-4-[(1-phenylethyl)amino]-1-piperidinecarboxylate in 170 parts of a hydrochloric acid solution 6N was stirred and refluxed for 45 hours. The reaction mixture was cooled and washed with dichloromethane. The aqueous phase was cooled in an ice-bath and treated with ammonium hydroxide. The product was extracted three times with 130 parts of dichloromethane. The combined extracts were washed with 10 parts of water, dried, filtered and evaporated. The residue was dissolved in methylbenzene and the latter was evaporated again, yielding 12.2 parts (100%) of (+)-cis-3-methoxy-N-(1-phenylethyl)-4-piperidinamine as a residue (intermediate 105).

Aufarbeitung

  1. temperaturerefluxed for 45 hours
  2. temperatureThe reaction mixture was cooled
  3. washwashed with dichloromethane
  4. temperatureThe aqueous phase was cooled in an ice-bath
  5. additiontreated with ammonium hydroxide
  6. extractionThe product was extracted three times with 130 parts of dichloromethane
  7. washThe combined extracts were washed with 10 parts of water
  8. customdried
  9. filtrationfiltered
  10. customevaporated
  11. dissolutionThe residue was dissolved in methylbenzene
  12. customthe latter was evaporated again

Quellen und Nachweise

ORD-Eintrag
ord-031340fc044243b088459ca76151d420
Quelldatensatz
uspto-grants-1992_08
Patentnummer
US05137896

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