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
DDD-025Parthasarathi Rajagopalan, WO2014137849 (to Daya Drug Discoveries Inc). Bonnecor Carbamazepine Carpipramine Ciclopramine Cianopramine Clomipramine & Clocapramine & Mosapramine Depramine Desipramine & Didesipramine [2095-95-6] Homopipramol Imipramine & Imipraminoxide Ketipramine Lofepramine Metapramine Opipramol Oxcarbazepine Quinupramine Trimipramine
Synthesis The synthesis of iminodibenzyl has been discussed:Huisgen, R., Laschtuvka, E., Bayerlein, F. (February 1960). "2.3;6.7‐Dibenzo‐azepin". Chemische Berichte. 93 (2): 392–397. doi:10.1002/cber.19600930219.Dr Walter Schindler & Dr Franz Haefliger, DE1035658 (1958 to Novartis AG, National Starch and Chemical Investment Holding Corp).Walter Dr Schindler & Franz Dr Haefliger, CH331207 (1958).Walter Dr. Raml, Gerhard Dr. Dipl.-Ing. Stern, Gerald Dipl.-Ing. Saischek, EP0158115 (1989 to Cl Pharma Aktiengesellschaft).Emil Pop, et al. RO78190 (1982).
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:Xu Weiling, Wang Lei, & Wang Jianjian, CN111253312 (2020 to Zhejiang Huazhou Pharmaceuti-cals Co ltd).Yan Wei, Wang Jikang, & Wang Guilin, CN1462739 (2003 to Zhejiang University of Technology ZJUT).Zou Zhenrong, CN102391182 (2012 to JIANGSU TONGHE PHARMACEUTICAL CO Ltd).马建泰 & 董正平, CN106588774 (2019 to Lanzhou University).位军辉, et al. CN108276409 (2018 to Zhejiang Ruibo Pharmaceutical Co Ltd, Zhejiang Jiuzhou Pharmaceutical Co Ltd).
References