Hepzidine

Hepzidine (INN) is a tricyclic antidepressant which was never marketed. It was first described by 1966.

Synthesis

The synthesis has been described in the chemical literature:

The reduction of dibenzosuberone (1) gives dibenzosuberol [1210-34-0] (2). This alcohol forms ethers exceedingly easily, probably via the carbonium ion. Treatment with N-methyl-4-piperidinol [106-52-5] (3) in the presence of acid gives hepzidine (4).

See also

• Diphenylpyraline is selfsame but is based on a benzhydrol aromatic pharmacophore.
• Dibenzosuberol is also used in the synthesis of Deptramine (DPH analog) as well as Oxitriptyline & Deptropine.

References