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【结 构 式】 
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【分子编号】44055 【品名】4-(6-chloro-7,8-dimethoxy-3-methyl-2,3,4,5-tetrahydro-1H-3-benzazepin-1-yl)phenyl methyl ether; 6-chloro-7,8-dimethoxy-1-(4-methoxyphenyl)-3-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine 【CA登记号】 |
【 分 子 式 】C20H24ClNO3 【 分 子 量 】361.8682 【元素组成】C 66.38% H 6.68% Cl 9.8% N 3.87% O 13.26% |
合成路线1
该中间体在本合成路线中的序号：(I)The optical resolution of the racemic 6-chloro-7,8-dimethoxy-1-(4-methoxyphenyl)-3-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine (I) (+)- or (-)-dibenzoyltartaric acid gives the corresponding (R)-isomer (II), which is N-demethylated by means of BrCN to yield 6-chloro-7,8-dimethoxy-1(R)-(4-methoxyphenyl)-3-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine (III). Finally, this compound is fully demethylated by treatment with BBr3. The optical resolution can also be performed by treatment of racemic (III) with (+)- or (-)-dibenzoyltartaric 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】 Webb, R.L.; Horodniak, J.W.; Dandridge, P.A.; Sarau, H.M.; Setler, P.E.; Weinstock, J.; Ackerman, D.M.; Kaiser, C.; Matz, E.D.; Stereoselectivity of some new dopamine receptor agonists. Acta Pharm Suec 1983, 2, 132-150. |
| 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) | 44055 | 4-(6-chloro-7,8-dimethoxy-3-methyl-2,3,4,5-tetrahydro-1H-3-benzazepin-1-yl)phenyl methyl ether; 6-chloro-7,8-dimethoxy-1-(4-methoxyphenyl)-3-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine | C20H24ClNO3 | 详情 | 详情 | |
| (II) | 44056 | (1R)-6-chloro-7,8-dimethoxy-1-(4-methoxyphenyl)-3-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine; 4-[(1R)-6-chloro-7,8-dimethoxy-3-methyl-2,3,4,5-tetrahydro-1H-3-benzazepin-1-yl]phenyl methyl ether | C20H24ClNO3 | 详情 | 详情 | |
| (III) | 44057 | (1R)-6-chloro-7,8-dimethoxy-1-(4-methoxyphenyl)-2,3,4,5-tetrahydro-1H-3-benzazepine; 4-[(1R)-6-chloro-7,8-dimethoxy-2,3,4,5-tetrahydro-1H-3-benzazepin-1-yl]phenyl methyl ether | C19H22ClNO3 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(I)The optical resolution of the racemic 6-chloro-7,8-dimethoxy-1-(4-methoxyphenyl)-3-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine (I) (+)- or (-)-dibenzoyltartaric acid gives the corresponding (S)-isomer (II), which is N-demethylated by means of BrCN to yield 6-chloro-7,8-dimethoxy-1(S)-(4-methoxyphenyl)-3-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine (III). Finally, this compound is fully demethylated by treatment with BBr3. The optical resolution can also be performed by treatment of racemic (III) with (+)- or (-)-dibenzoyltartaric acid.
| 【1】 Webb, R.L.; Horodniak, J.W.; Dandridge, P.A.; Sarau, H.M.; Setler, P.E.; Weinstock, J.; Ackerman, D.M.; Kaiser, C.; Matz, E.D.; Stereoselectivity of some new dopamine receptor agonists. Acta Pharm Suec 1983, 2, 132-150. |
| 【2】 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) | 44055 | 4-(6-chloro-7,8-dimethoxy-3-methyl-2,3,4,5-tetrahydro-1H-3-benzazepin-1-yl)phenyl methyl ether; 6-chloro-7,8-dimethoxy-1-(4-methoxyphenyl)-3-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine | C20H24ClNO3 | 详情 | 详情 | |
| (II) | 44058 | 4-[(1S)-6-chloro-7,8-dimethoxy-3-methyl-2,3,4,5-tetrahydro-1H-3-benzazepin-1-yl]phenyl methyl ether; (1S)-6-chloro-7,8-dimethoxy-1-(4-methoxyphenyl)-3-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine | C20H24ClNO3 | 详情 | 详情 | |
| (III) | 44059 | (1S)-6-chloro-7,8-dimethoxy-1-(4-methoxyphenyl)-2,3,4,5-tetrahydro-1H-3-benzazepine; 4-[(1S)-6-chloro-7,8-dimethoxy-2,3,4,5-tetrahydro-1H-3-benzazepin-1-yl]phenyl methyl ether | C19H22ClNO3 | 详情 | 详情 |