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

HRID 1287631Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1287631
[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 2 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-70bfb31f5b2d42e5a2765bfbb17458ab
Quelldatensatz
uspto-grants-1976_10
Patentnummer
US03985751

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