SYNTHESIS, STRUCTURAL AND CONFORMATIONAL STUDY OF NEW AMIDES DERIVED FROM 2-METHYL-2-AZABICYCLO[2.2.2]OCTAN-5 SYN (ANTI) AMINES

A series of amides derived from spn and anti 2-methyl-2-azabicyclo[2.2 .2]octan-5-amines has been synthesized and studied by IR, Raman, H-1 a nd C-13 NMR spectroscopy. The crystal structure of (4-quinolinecarboxa mide)-2-azabicyclo[2.2.2]octane Id has been determined by X-ray diffra ction. It has been found that gn amides present a preferred conformati on in CDCl3 solution, with the CH3-N bond in exo position. This is als o observed for compound Id in the solid state. However, for anti amide s the CH3-N bond adopts a favoured endo position. A conformational ana lysis using molecular modelling techniques was undertaken in order to gain additional information. (C) 1997 Elsevier Science B.V.