Synthesis of sterically hindered 1-arylpyrrolidines and 1-arylpiperidines by condensation of primary aromatic amines with cyclic ethers or diols |
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Authors: | Robert E Walkup Scott Searles |
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Institution: | Department of Chemistry, University of Missouri-Columbia Columbia, MissouriUSA 65211 |
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Abstract: | A variety of 1-(-alkylphenyl)- and 1-(-'-dialkylphenyl)- pyrrolidines and -piperidines were prepared by the gas phase alumina mediated condensation of tetrahydrofuran (THF), tetrahydropyran (THP) or the corresponding diols with primary aromatic amines in fair to high yield. This methodology can also be used for the synthesis of 1-phenylhexahydroazepine from aniline. A mechanistic interpretation of the catalytic action of alumina is presented. |
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Keywords: | Current address: Sandoz Research Institute Sandoz Inc E Hanover New Jersey USA 07936 |
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