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【结 构 式】 
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【分子编号】12465 【品名】6,11-Dihydro-5H-dibenzo[b,e]azepin-6-ylmethylamine; 6,11-Dihydro-5H-dibenzo[b,e]azepin-6-ylmethanamine 【CA登记号】 |
【 分 子 式 】C15H16N2 【 分 子 量 】224.30552 【元素组成】C 80.32% H 7.19% N 12.49% |
合成路线1
该中间体在本合成路线中的序号：(I)By cyclization of 6-(aminomethyl)-6,11-dihydro-5H-dibenz[b,e]azepine (I) with cyanogen bromide (II) in THF, followed by a treatment with NaOH and acidification with HCl in ether.
| 【1】 Walther, G.; Schneider, C.S,, Weber, K.-H.; Fuegner, A. (Boehringer Ingelheim GmbH); Fused dibenzo imidazolo compounds, compositions and use. DE 3008944 . |
| 【2】 Serradell, M.N.; Castaner, J.; Epinastine Hydrochloride. Drugs Fut 1987, 12, 12, 1106. |
合成路线2
该中间体在本合成路线中的序号：(III)A new synthesis of epinastine hydrochloride has been described: The reaction of 6-chloro-11H-dibenzo[b,e]azepine (I) with NaCN in DMSO at 90 C gives 11H-dibenzo[b,e]azepine-6-carbonitrile (II), which is reduced with AlH3 (prepared from LiAlH4 and H2SO4 in THF) in THF to afford 6-(aminomethyl)-6,11-dihydro-5H-dibenzo[b,e]azepine (III). Finally, this compound is cyclized with cyanogen bromide in THF and treated with HCl.
| 【1】 Walther, G.; Bechtel, W.D.; Daniel, H.; Brandt, K.; New tetracyclic guanidine derivatives with H1-antihistaminic properties. Chemistry of epinastine. Arzneim-Forsch Drug Res 1990, 40, 4, 440-6. |
合成路线3
该中间体在本合成路线中的序号：(VI)
| 【1】 Kawahan H, Mori M, etal.2002. Preparation of 6-aminomethyl-6,11-dihydro-5H-dibenzo[b.e]azepine as intermediate for epinastine, hydrochloride,antiallergyagent. JP 2002308851 |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 62393 | 2-benzylaniline; 2-benzylphenylamine | 28059-64-5 | C13H13N | 详情 | 详情 |
| (II) | 66338 | 2-benzyl-N-(3-chloroprop-1-en-2-yl)aniline | C16H16ClN | 详情 | 详情 | |
| (III) | 62395 | 6-(chloromethyl)-11H-dibenzo[b,e]azepine | 21535-44-4 | C15H12ClN | 详情 | 详情 |
| (IV) | 66339 | 2-((11H-dibenzo[b,e]azepin-6-yl)methyl)isoindoline-1,3-dione | C23H16N2O2 | 详情 | 详情 | |
| (V) | 66340 | 6-(Phthalimidomethyl)-6,11-dihydro-5H-dibenz[b,e]azepine | 143878-20-0 | C23H18N2O2 | 详情 | 详情 |
| (VI) | 12465 | 6,11-Dihydro-5H-dibenzo[b,e]azepin-6-ylmethylamine; 6,11-Dihydro-5H-dibenzo[b,e]azepin-6-ylmethanamine | C15H16N2 | 详情 | 详情 | |
| (VII) | 10926 | (1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)potassium | C8H4KNO2 | 详情 | 详情 |