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【结 构 式】 
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【分子编号】44621 【品名】6-chloro-7,8-dimethoxy-1-(4-methoxyphenyl)-2,3,4,5-tetrahydro-1H-3-benzazepine; 4-(6-chloro-7,8-dimethoxy-2,3,4,5-tetrahydro-1H-3-benzazepin-1-yl)phenyl methyl ether 【CA登记号】 |
【 分 子 式 】C19H22ClNO3 【 分 子 量 】347.84132 【元素组成】C 65.61% H 6.37% Cl 10.19% N 4.03% O 13.8% |
合成路线1
该中间体在本合成路线中的序号：(VII)The bromination of labeled 4'-methoxyacetophenone (I) with CuBr2 gives 4'-methoxyphenacyl bromide (II), which is reduced with NaBH4, yielding the carbinol (III). The protection of (III) with DHP affords the tetrahydropyranyl ether (IV), which is condensed with 2-(2-chloro-3,4-dimethoxyphenyl)ethylamine (V) and acidified to provide the aminoalcohol (VI). The cyclization of (VI) with MsOH and trifluoroacetic acid furnishes labeled 6-chloro-7,8-dimethoxy-1-(4-methoxyphenyl)-2,3,4,5-tetrahydro-1H-3-benzazepine (VII), which is finally demethylated with BBr3 and MsOH.
| 【1】 Hieble, J.P.; Wilson III, J.W.; Weinstock, J.; The chemistry and pharmacology of 3-benzazepines derivatives. Drugs Fut 1985, 10, 8, 645. |
| 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) | 11041 | 4-Methoxyacetophenone; 1-(4-Methoxyphenyl)-1-ethanone | 100-06-1 | C9H10O2 | 详情 | 详情 |
| (I) | 44616 | 1-(4-methoxyphenyl)-1-ethanone | C9H10O2 | 详情 | 详情 | |
| (II) | 21991 | 2-Methoxyphenacyl bromide; 2-bromo-1-(4-methoxyphenyl)-1-ethanone | 2632-13-5 | C9H9BrO2 | 详情 | 详情 |
| (II) | 44617 | 2-bromo-1-(4-methoxyphenyl)-1-ethanone | C9H9BrO2 | 详情 | 详情 | |
| (III) | 44053 | 2-bromo-1-(4-methoxyphenyl)-1-ethanol | C9H11BrO2 | 详情 | 详情 | |
| (III) | 44618 | 2-bromo-1-(4-methoxyphenyl)-1-ethanol | C9H11BrO2 | 详情 | 详情 | |
| (IV) | 44054 | 2-bromo-1-(4-methoxyphenyl)ethyl tetrahydro-2H-pyran-2-yl ether; 2-[2-bromo-1-(4-methoxyphenyl)ethoxy]tetrahydro-2H-pyran | C14H19BrO3 | 详情 | 详情 | |
| (IV) | 44619 | 2-bromo-1-(4-methoxyphenyl)ethyl tetrahydro-2H-pyran-2-yl ether; 2-[2-bromo-1-(4-methoxyphenyl)ethoxy]tetrahydro-2H-pyran | C14H19BrO3 | 详情 | 详情 | |
| (V) | 42037 | 2-chloro-3,4-dimethoxyphenethylamine; 2-(2-chloro-3,4-dimethoxyphenyl)-1-ethanamine | 67287-36-9 | C10H14ClNO2 | 详情 | 详情 |
| (VI) | 31702 | 2-[(2-chloro-3,4-dimethoxyphenethyl)amino]-1-(4-methoxyphenyl)-1-ethanol | C19H24ClNO4 | 详情 | 详情 | |
| (VI) | 44620 | 2-[(2-chloro-3,4-dimethoxyphenethyl)amino]-1-(4-methoxyphenyl)-1-ethanol | C19H24ClNO4 | 详情 | 详情 | |
| (VII) | 31704 | 4-(6-chloro-7,8-dimethoxy-2,3,4,5-tetrahydro-1H-3-benzazepin-1-yl)phenyl methyl ether; 6-chloro-7,8-dimethoxy-1-(4-methoxyphenyl)-2,3,4,5-tetrahydro-1H-3-benzazepine | C19H22ClNO3 | 详情 | 详情 | |
| (VII) | 44621 | 6-chloro-7,8-dimethoxy-1-(4-methoxyphenyl)-2,3,4,5-tetrahydro-1H-3-benzazepine; 4-(6-chloro-7,8-dimethoxy-2,3,4,5-tetrahydro-1H-3-benzazepin-1-yl)phenyl methyl ether | C19H22ClNO3 | 详情 | 详情 |