Iminodibenzyl

Iminodibenzyl is an aromatic organic compound with a multitude of uses in medicinal chemistry. Iminodibenzyl is a fundamental building block used mainly in the construction of tricyclic antidepressants. 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

1. DDD-025
2. Bonnecor
3. Carbamazepine
4. Carpipramine
5. Ciclopramine
6. Cianopramine
7. Clomipramine & Clocapramine & Mosapramine
8. Depramine
9. Desipramine & Didesipramine [2095-95-6]
10. Homopipramol
11. Imipramine & Imipraminoxide
12. Ketipramine
13. Lofepramine
14. Metapramine
15. Opipramol
16. Oxcarbazepine
17. Quinupramine
18. Trimipramine

Synthesis

The synthesis of iminodibenzyl has been discussed:

The treatment of 2-Nitrotoluene [88-72-2] (1) with amyl nitrite or Isopentyl formate [110-45-2] and potassium tert-butoxide resulted in an “oxidative coupling” to give 2,2'-Dinitrodibenzyl [16968-19-7] (2). Catalytic hydrogenation of both nitro groups gives 2,2'-Ethylenedianiline [34124-14-6] (4). Treatment with phosphoric acid then completes the synthesis of iminodibenzyl (5).

Additional Chinese patents:

References