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

HRID 972957Notes

Reaction equation

HRID 972957 reaction equation
[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

Participants

6

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 176Acetic AcidSolventHCID 241BenzeneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-23a835972c114adcbaed8a2cac7c8ab1
Source dataset
uspto-grants-1977_10
Patent number
US04054569

Reaction notes

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