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cis- and trans-2-(3,4,5-trimethoxyphenyl)cyclohexylamines: N-methyl and N,N-dimethyl derivatives

✍ Scribed by Betty R. Lowry; Alain C. Huitric

Publisher
John Wiley and Sons
Year
1971
Tongue
English
Weight
266 KB
Volume
60
Category
Article
ISSN
0022-3549

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✦ Synopsis

The N-methyl and N,N-dimethyl derivatives of cisand rruns-2-( 3,4,5-trimethoxyphenyl)cyclohexylamines were prepared for evaluation of psychotropic activity. Synthesis by catalytic reductive methylation and characterization by NMR spectroscopy are reported. Magnetic nonequivalence of the methyl groups was observed in the trans-N,N-dimethyl derivative under acidic conditions where inversion of the nitrogen atom is suppressed. Keyphrases 0 2-(3,4,5-Trimethoxyphenyl)cyclohexylamines, cis and trans-N-methyl and N,N-dimethyl derivatives, synthesis as potential psychotropic agents 0 TLC-analysis 0 NMR-structure * This suppression of inversion in the acidic medium is indicated from the observed coupling between the ammonium and N C H s protons which requires a slow N-H proton exchange on the NMR time scale.

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The con6gurations and conformations of cis-and tram-N-methyl-and -N-benzyl-4,5-and -5,6tetramethylenetetrahydm-l,3-o~es were determined by 'H and -C NMR spectroscopy. The cis isomers are conformationally homogeneous, having the hetero atom attached to the cydohexyl ring, in the axial and equatorial