Ethyl 4-oxo-1-piperidinecarboxylate → ethyl 1,3,4,5-tetrahydro-8-(phenylmethoxy)-2H-pyrido[4,3-b]indole-2-carboxylate

HRID 1634180

Reaktionsgleichung

Reaktionsgleichung von HRID 1634180
O=[C:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][CH2:3]1.[CH2:13]([O:20][C:21]1[CH:26]=[CH:25][C:24]([NH:27]N)=[CH:23][CH:22]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(O)C>[C:14]1([CH2:13][O:20][C:21]2[CH:26]=[CH:25][C:24]3[NH:27][C:2]4[CH2:7][CH2:6][N:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][C:3]=4[C:23]=3[CH:22]=2)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Komponenten

4

Edukt 2

HCID 34767Ethyl 4-oxo-1-piperidinecarboxylateHCID 5613924-Benzyloxyphenylhydrazine

Produkt 1

HCID 18677416ethyl 1,3,4,5-tetrahydro-8-(phenylmethoxy)-2H-pyrido[4,3-b]indole-2-carboxylateAusbeute 63,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A mixture of ethyl 4-oxo-1-piperidinecarboxylate (0.23 mol) and 4-(benzyloxy)-phenyl hydrazine (0.23 mol) in ethanol (400 ml) was stirred and refluxed for 5 hours. The reaction mixture was stirred overnight at room temperature. The solid was filtered off and washed on filter with H2O/2-propanol (200 ml). The precipitate was dissolved in CHCl3 (300 ml), washed with water (2×50 ml), dried, filtered and the solvent was evaporated. The residue was crystallized from CH3CN (300 ml) and cooled to 0° C. The resulting precipitate was filtered off and dried, yielding 51.0 g (63%) of ethyl 1,3,4,5-tetrahydro-8-(phenylmethoxy)-2H-pyrido[4,3-b]indole-2-carboxylate (intermediate 1).

Aufarbeitung

  1. temperaturerefluxed for 5 hours
  2. stirringThe reaction mixture was stirred overnight at room temperature
  3. filtrationThe solid was filtered off
  4. washwashed
  5. filtrationon filter with H2O/2-propanol (200 ml)
  6. dissolutionThe precipitate was dissolved in CHCl3 (300 ml)
  7. washwashed with water (2×50 ml)
  8. customdried
  9. filtrationfiltered
  10. customthe solvent was evaporated
  11. customThe residue was crystallized from CH3CN (300 ml)
  12. filtrationThe resulting precipitate was filtered off
  13. customdried

Quellen und Nachweise

ORD-Eintrag
ord-4fcb784bbd514a9490ecda8ef8405621
Quelldatensatz
uspto-grants-2003_01
Patentnummer
US06506768B2

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