Abstract
The triketones3–6 were obtained by alkylation of cyclopentanone or cyclohexanone with the appropriate cycloalkanone bis-Mannich base (1) or (2). Schmidt reaction of the tricketones3–6 afforded the corresponding tricyclic lactames7–10 respectively. Reduction of7 and9 gave compounds11 and12 respectively.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
Literature Cited
Afsah, E. M., Metwally, M. A. and Khalifa, M. M., Synthesis of 2,5-Bis(piperidinomethyl)piperidine and 1,5-Bis(aminomethyl)-3-azabicyclo[3.2.1]octanones.Monatsh. Chem., 115, 303 (1984).
Austin, E. M., Brown, H. L. and Buchanan, G. L., The thermal Michael reaction-III The scope of the reaction.Tetrahedron, 25, 5509 (1969).
Birkofer, L. and Engels, H. D., 8a, 9a-Diazaperhydroanthracene from di(2-piperidon-6-yl)methane.Chem. Ber., 95, 2212 (1962).
Brown, H. L., Buchanan, G. L., Curran, A. C. W. and McLay, G. W., The thermal Michael reaction-I orientation features.Tetrahedron, 24, 4565 (1968).
Hammounda, M., Hamama, W. S. and Afsah, E. M., Synthesis of 3-[(2′-piperidyl and 2′-homopipperidyl) methyl]-tetrahydro-2-benzazepines and related compounds.J. Prakt. Chem., 329, 520 (1987).
Hamama, W. S., Hammouda, M. and Afsah, E. M., Mannich reaction with 5,5-dimethyl-3-phenylamino-2-cyclohexen-1-one.Z. Naturforsch., 43b, 483 (1988).
Schmid, H. J., Hunger, A. and Hoffmann, K., Steric and electrostatic effects in the Schmidt reaction.Helv. Chim. Acta 39, 607 (1956).
Windholz, M.,The Merck Index, 9th ed., Merck, Rahway, 1976, Monograph No. 2470, 7699, 7279 and 2471.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Hammouda, M., Kandeel, EeD., Hamama, W. et al. Synthesis of 2,5-bis(2′-piperidylmethyl) piperidine and related compounds. Arch. Pharm. Res. 16, 68–70 (1993). https://doi.org/10.1007/BF02974131
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF02974131