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

Article abstract of DOI:10.1016/S0022-2860(96)09561-0

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 N-CH₃ 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.