Protriptyline, N-methyl-5-H-dibenzo[a,d]cyclohepten-5-propylamine (7.1.22),
differs from all of the drugs described above in that there is present a double bond at the
C10¨CC11 position of the central 7-membered ring of the tricyclic part of the molecule. At
the same time, a free electron pair on C5 belonging to either a nitrogen atom or an exocyclic double bond are excluded, which undoubtedly changes both the architecture of the
whole molecule as well as, the collocation of pharmacophore groups.
Protriptyline is synthesized by alkylation of 5-H-dibenzo[a,d]cycloheptene with 3-(Nphormyl-N-methylamino)propylchloride (7.1.20), which is synthesized from compound
(7.1.19). The resulting intermediate product (7.1.21) undergoes alkaline hydrolysis, which
leads to the formation of protriptyline (7.1.21) [33¨C38].
