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【结 构 式】 
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【分子编号】39207 【品名】7,8-dimethoxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine; 8-methoxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl methyl ether 【CA登记号】 |
【 分 子 式 】C18H21NO2 【 分 子 量 】283.37028 【元素组成】C 76.3% H 7.47% N 4.94% O 11.29% |
合成路线1
该中间体在本合成路线中的序号：(IV)By condensation of styrene oxide (I) with 3,4-dimethoxyphenylethylamine (II) at 100 C to give N-(beta-hydroxy-beta-phenyl)ethyl-2-(3',4'-dimethoxyphenyl)ehtylamine (III), which is cyclized with H2SO4 to 1-phenyl-7,8-dimethoxy-2,3,4,5-tetrahydro-3,1-benzazepine (IV). This product is finally methylated with a refluxing mixture of formaldehyde and formic acid.
| 【1】 Hieble, J.P.; Wilson III, J.W.; Weinstock, J.; The chemistry and pharmacology of 3-benzazepines derivatives. Drugs Fut 1985, 10, 8, 645. |
| 【2】 Walter, L.A.; Chang, W.K. (Schering Corp.); Novel benzazepines. US 3393192 . |
| 【3】 Castaner, J.; Thorpe, P.; Trimopam. Drugs Fut 1976, 1, 4, 194. |
| 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) | 23017 | 2-phenyloxirane | 96-09-3 | C8H8O | 详情 | 详情 |
| (II) | 10098 | 2-(3,4-Dimethoxyphenyl)-1-ethanamine; 3,4-Dimethoxyphenethylamine; 2-(3,4-Dimethoxyphenyl)ethylamine | 120-20-7 | C10H15NO2 | 详情 | 详情 |
| (III) | 39206 | 2-[(3,4-dimethoxyphenethyl)amino]-1-phenyl-1-ethanol | C18H23NO3 | 详情 | 详情 | |
| (IV) | 39207 | 7,8-dimethoxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine; 8-methoxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl methyl ether | C18H21NO2 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(IV)The condensation of 3,4-dimethoxyphenethylamine (I) with styrene oxide (II) by heating at 100 C gives N-[2-(3,4-dimethoxyphenyl)ethyl]-2-phenyl-2-hydroxyethylamine (III), which can be cyclized with H2SO4 in refluxing trifluoroacetic acid yielding 2,3,4,5-tetrahydro-7,8-dimethoxy-1-phenyl-1H-3-benzazepine (IV). Finally, intermediate (IV) is demethylated with refluxing 48% HBr (III) can also by cyclized and demethylated simultaneously by refluxing with 48% HBr.
| 【1】 Kaiser, C.; et al.; DE 2629887 . |
| 【2】 Hieble, J.P.; Wilson III, J.W.; Weinstock, J.; The chemistry and pharmacology of 3-benzazepines derivatives. Drugs Fut 1985, 10, 8, 645. |
| 【3】 Castaner, J.; Hillier, K.; SKF-38393. Drugs Fut 1980, 5, 10, 507. |
| 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) | 10098 | 2-(3,4-Dimethoxyphenyl)-1-ethanamine; 3,4-Dimethoxyphenethylamine; 2-(3,4-Dimethoxyphenyl)ethylamine | 120-20-7 | C10H15NO2 | 详情 | 详情 |
| (II) | 23017 | 2-phenyloxirane | 96-09-3 | C8H8O | 详情 | 详情 |
| (III) | 39206 | 2-[(3,4-dimethoxyphenethyl)amino]-1-phenyl-1-ethanol | C18H23NO3 | 详情 | 详情 | |
| (IV) | 39207 | 7,8-dimethoxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine; 8-methoxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl methyl ether | C18H21NO2 | 详情 | 详情 |