1,3,4-Trisubstituted-4-arylpiperidines and their preparation

Details 1,3,4-Trisubstituted-4-arylpiperidines and their preparation 1,3,4-Trisubstituted-4-arylpiperidines and their preparation

1976-05-27

1978-03-28

Jiles, Henry R.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

26029368, 26029364, 26029372, 26029373, 26029377, 26029379, 2602938, 26029382, 26029383, 26029384, 26029381, 260290H, 260297R, 424267, C07D41906

Patent

active

040814505

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:
patent: 1915334 (1933-06-01), Salzberg et al.
patent: 2075359 (1937-03-01), Salzberg et al.
patent: 2892842 (1959-06-01), McElvain
patent: 3080372 (1963-03-01), Janssen
patent: 3936468 (1976-02-01), Yamamoto et al.
McElvain et al. "J. Am. Chem. Soc.," vol. 80, pp. 3915-3923 (1958).
Janssen "Int. J. Neuropharmacology" vol. 1, pp. 145-148 (1962).

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