Chemistry of carbon compounds – Miscellaneous organic carbon compounds – C-metal
Patent
1977-11-17
1978-09-19
Trousof, Natalie
Chemistry of carbon compounds
Miscellaneous organic carbon compounds
C-metal
26029354, 2603265M, 2603268, 26032687, C07D20952
Patent
active
041154002
ABSTRACT:
Novel 1,3,4-trisubstituted-4-arylpiperidines are prepared by alkylating a 2,3-disubstituted-3-arylpyrroline to afford a 1,2,3-trisubstituted-3-aryl-1-pyrrolinium salt, reacting the salt with diazomethane to provide a 1,2,3-trisubstituted-3-aryl-1,2-methylene-pyrrolidinium salt, heating the pyrrolidinium salt to effect a ring expansion to the corresponding 1,3,4-trisubstituted-4-aryl-1,4,5,6-tetrahydropyridinium salt, neutralizing the salt and reducing the tetrahydropyridine to provide a 1,3,4-trisubstituted-4-arylpiperidine. The piperidines so formed are useful as pharmacological agents and as intermediates in the preparation of other piperidines of the invention. The compounds provided herein are especially useful as narcotic agonists analgesics and as narcotic antagonists.
REFERENCES:
Chemical Abstracts, 76:71797v, (1972), [Hammer, C. et al., Tetrahedron 1972, 28(2), 239-253].
Ashbrook Charles W.
Eli Lilly and Company
Schwartz Richard A.
Smith Everet F.
Trousof Natalie
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