Iminodibenzyl is an aromatic organic compound with a multitude of uses in

medicinal chemistry Medicinal or pharmaceutical chemistry is a scientific discipline at the intersection of chemistry and pharmacy involved with drug design, designing and developing pharmaceutical medication, drugs. Medicinal chemistry involves the identification, ...

. Iminodibenzyl is a fundamental building block used mainly in the construction of

tricyclic antidepressants Tricyclic antidepressants (TCAs) are a class of medications that are used primarily as antidepressants. TCAs were discovered in the early 1950s and were marketed later in the decade. They are named after their chemical structure, which contains ...

. Chemically speaking, it is almost the same as for iminostilbene, but differs in that the 2 carbon bridge between the two phenyl rings is saturated (with hydrogen), and does not contain an olefin.

Applications

# DDD-025 # Bonnecor #

Carpipramine Carpipramine (Prazinil, Defekton) is an atypical antipsychotic used for the treatment of schizophrenia and anxiety in France and Japan. In addition to its neuroleptic and anxiolytic effects, carpipramine also has hypnotic properties. It is struct ...

# Cianopramine etc.

Synthesis

The synthesis of iminodibenzyl has been discussed: Iminodibenzyl synthesis

The treatment of

2-Nitrotoluene 2-Nitrotoluene or ''ortho''-nitrotoluene is an organic compound with the formula CH3C6H4NO2. It is pale yellow liquid that crystallizes in two forms, called α (−9.27 °C) and β (−3.17 °C). It is mainly a precursor to o-toluidine, which is ...

8-72-2(1) with amyl nitrite or Isopentyl formate 10-45-2and potassium tert-butoxide resulted in an “oxidative coupling” to give 2,2'-Dinitrodibenzyl 6968-19-7(2).

Catalytic hydrogenation Hydrogenation is a chemical reaction between molecular hydrogen (H2) and another compound or element, usually in the presence of a catalyst such as nickel, palladium or platinum. The process is commonly employed to reduce or saturate organic ...

of both nitro groups gives 2,2'-Ethylenedianiline 4124-14-6(4). Treatment with

phosphoric acid Phosphoric acid (orthophosphoric acid, monophosphoric acid or phosphoric(V) acid) is a colorless, odorless phosphorus-containing solid, and inorganic compound with the chemical formula . It is commonly encountered as an 85% aqueous solution, ...

then completes the synthesis of iminodibenzyl (5). Additional Chinese patents:位军辉, et al. CN108276409 (2018 to Zhejiang Ruibo Pharmaceutical Co Ltd, Zhejiang Jiuzhou Pharmaceutical Co Ltd).

References

{{Chemical classes of psychoactive drugs

Dibenzazepines Dibenzazepine (iminostilbene) is a chemical compound with two benzene rings fused to an azepine ring. Many pharmaceuticals, such as carbamazepine, oxcarbazepine, and depramine, are based on a dibenzazepine structure. See also * Benzazepine * D ...

Tricyclic antidepressants Aromatic amines Nitrogen heterocycles