Synthesis, structural and conformational study of some ureas derived from 3-methyl-2,4-diphenyl-3-azabicyclo[3.3.1]nonan-9α-amine

A series of ureas derived from 3-methyl-2,4-diphenyl-3-azabicyclo[3.3.1]nonan-9α-amine were synthesized and studied by IR, Raman, 1H and 13C NMR spectroscopy. These compounds adopt, in CDCl3, a preferred flattened chair-chair conformation with the cyclohexane ring more flattened than the piperidine moiety and the NCH3 groups in equatorial positions. IR and 1H and 13C NMR data show the presence of two conformations at the urea unity. These results are supported by molecular modeling studies.Peer reviewe