Ethyl 5-aminovalerate → N-[(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl)methyl]-2-piperidone

HRID 972957Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 972957
[CH:1]1[C:11]2[CH2:10][CH2:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[CH:6]([CH:16]=O)[C:5]=2[CH:4]=[CH:3][CH:2]=1.C(O[C:21](=[O:27])[CH2:22][CH2:23][CH2:24][CH2:25][NH2:26])C>C(O)(=O)C.C1C=CC=CC=1.[Zn]>[CH:1]1[C:11]2[CH2:10][CH2:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[CH:6]([CH2:16][N:26]3[CH2:25][CH2:24][CH2:23][CH2:22][C:21]3=[O:27])[C:5]=2[CH:4]=[CH:3][CH:2]=1

Komponenten

6

Edukt 2

HCID 11469139Ethyl 5-aminovalerateHCID 1495090410,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-carboxaldehyde

Produkt 1

HCID 21402982N-[(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl)methyl]-2-piperidone

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23994ZincKatalysatorHCID 176Acetic AcidLösungsmittelHCID 241BenzeneLösungsmittel

Versuchsvorschrift

By subjecting a mixture of 10,11-dihydro-5H-dibenzo-[a,d]cycloheptene-5-carboxaldehyde (2.2 g), described in Example 168, and 5-aminovaleric acid ethyl ester (1.45 g) and zinc dust (3.0 g) in 3.0 ml of acetic acid and 100 ml of benzene, to a two hour reflux, followed by removal of the excess zinc by filtration, addition of dilute sodium hydroxide solution to render the mixture alkaline and extraction with benzene affords the cyclic amide, N-[(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl)methyl]-2-piperidone, γmaxCHCl3 1650 cm-1, as an oil. Further treatment of this oil according to the conditions of the Bischler-Napieralski reaction described in Example 2, yields a product identical with the quaternary salt, 1,3,4,5,6,10,11,15b-octahydrobenzo[6,7]cyclohepta[1,2,3-de]pyrido[2,1-a]isoquinolinium chloride obtained in Example 2.

Aufarbeitung

  1. temperaturereflux
  2. customfollowed by removal of the excess zinc by filtration, addition of dilute sodium hydroxide solution to render
  3. extractionthe mixture alkaline and extraction with benzene

Quellen und Nachweise

ORD-Eintrag
ord-23a835972c114adcbaed8a2cac7c8ab1
Quelldatensatz
uspto-grants-1977_10
Patentnummer
US04054569

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