Abstract:
Ohmefentanyl,
N-1-(2-hydroxyl-2 phenyl)-3-methyl-piperidyl-
N-phenylpropanamide,is a new and potent analgesic agent.Two stereoisomers :
cis-(3
R,4
S,2′
R)-ohmefentanyl(Ⅰ) and
trans-( 3
R,4
R,2′
S)-ohmefentanyl(Ⅱ),were selected for X-Ravcrystallographic study.The two isomers were shown tO have an sp
3N(1)and an sp
2N(7) and thepiperidine ring has a chair conformation,The
cis-isomerⅠhas an axial 3-methyl with an equatorial 4-
N-phenylpropanamide group, while the two groups of the
trans-isomer Ⅱ are all equatorial. In Ⅰmolecule , the plane formed by the 4-propanamide group and atom C(4)is almost perpendicular to the4-
N-phenyl ring plane; in Ⅱ, the dihedral angle of the two planes is about 100°. Intramolecularhydrogen bond of O(1)一H…N(1) occurs in both the two isomers and isomer Ⅱ is also involved inintermolecular hydrogen bond O(1)一H(A)…O(2)(B).