Iminodibenzyl

Iminodibenzyl

Names
Other names 10,11-Dihydro-5H-dibenzo[b,f]azepine
Identifiers
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL63054
ChemSpider	9886
ECHA InfoCard	100.007.080
EC Number	207-787-1
PubChem CID	10308
UNII	262BX7OE3U
CompTox Dashboard (EPA)	DTXSID8049414
InChI InChI=1S/C14H13N/c1-3-7-13-11(5-1)9-10-12-6-2-4-8-14(12)15-13/h1-8,15H,9-10H2 Key: ZSMRRZONCYIFNB-UHFFFAOYSA-N
SMILES C1CC2=CC=CC=C2NC3=CC=CC=C31
Properties
Chemical formula	C14H13N
Molar mass	195.26 g/mol
Density	g/cm3 (20°C)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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. Carpipramine
4. Cianopramine etc.

Synthesis

The synthesis of iminodibenzyl has been discussed: ^{[1] [2] [3] [4] [5]}

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: ^{[6] [7] [8] [9] [10]}

References

1. 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.
2. Dr Walter Schindler & Dr Franz Haefliger, DE1035658 (1958 to Novartis AG, National Starch and Chemical Investment Holding Corp).
3. Walter Dr Schindler & Franz Dr Haefliger, CH331207 (1958).
4. Walter Dr. Raml, Gerhard Dr. Dipl.-Ing. Stern, Gerald Dipl.-Ing. Saischek, EP0158115 (1989 to Cl Pharma Aktiengesellschaft).
5. Emil Pop, et al. RO78190 (1982).
6. Xu Weiling, Wang Lei, & Wang Jianjian, CN111253312 (2020 to Zhejiang Huazhou Pharmaceuti-cals Co ltd).
7. Yan Wei, Wang Jikang, & Wang Guilin, CN1462739 (2003 to Zhejiang University of Technology ZJUT).
8. Zou Zhenrong, CN102391182 (2012 to JIANGSU TONGHE PHARMACEUTICAL CO Ltd).
9. 马建泰 & 董正平, CN106588774 (2019 to Lanzhou University).
10. 位军辉, et al. CN108276409 (2018 to Zhejiang Ruibo Pharmaceutical Co Ltd, Zhejiang Jiuzhou Pharmaceutical Co Ltd).