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【结 构 式】 
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【药物名称】EMD-23448 【化学名称】3-[4-(4-Phenyl-1,2,3,6-tetrahydro-1-pyridyl)butyl]indole 【CA登记号】73966-53-7, 73966-59-3 (HCl) 【 分 子 式 】C23H26N2 【 分 子 量 】330.47707 |
【开发单位】Merck KGaA (Originator) 【药理作用】Dopamine Receptor Agonists |
合成路线1
The reaction of 4-(3-indolyl)butyric acid (I) with 4-phenyl-3,4-dehydropiperidine (II) by means of carbonyldiimidazole (A) in THF gives 3-[4-oxo-4-(4-phenyl-3,4-dehydro-1-piperidyl)butyl]indole (III), which is reduced with LiAlH4 in THF.
| 【1】 Hausberg, H.H.; Koppe, V.; Poetsch, E.; Saiko, O.; Seyfried, C.; US 4251538 . |
| 【2】 Blancafort, P.; Hillier, K.; Serradell, M.N.; Castaner, J.; EMD-23,448. Drugs Fut 1983, 8, 5, 400. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (A) | 11353 | 1,1'-Carbonyldiimidazole; Di(1H-imidazol-1-yl)methanone; N,N-Carbonyldiimidazole; 1,1'-Carbonylbis(1H-imidazole) | 530-62-1 | C7H6N4O | 详情 | 详情 |
| (I) | 26532 | Indole-3-butyric acid; 4-(3-Indolyl)butyric acid; 4-(1H-Indol-3-yl)butyric acid | 133-32-4 | C12H13NO2 | 详情 | 详情 |
| (II) | 13002 | 4-Phenyl-1,2,3,6-tetrahydropyridine; 1,2,3,6-Tetrahydro-4-phenyl-pyridine | 10338-69-9 | C11H13N | 详情 | 详情 |
| (III) | 36089 | 4-(1H-indol-3-yl)-1-[4-phenyl-3,6-dihydro-1(2H)-pyridinyl]-1-butanone | C23H24N2O | 详情 | 详情 |
合成路线2
By condensation of (II) with 3-(4chlorobutyl)indole (IV) in acetonitrile. Other compounds with Br, I or tosyloxy substituents instead of Cl can also be used in the above mentioned synthesis.
| 【1】 Hausberg, H.H.; Koppe, V.; Poetsch, E.; Saiko, O.; Seyfried, C.; US 4251538 . |
| 【2】 Blancafort, P.; Hillier, K.; Serradell, M.N.; Castaner, J.; EMD-23,448. Drugs Fut 1983, 8, 5, 400. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (IVa) | 36090 | 4-(1H-indol-3-yl)butyl 4-methylbenzenesulfonate | C19H21NO3S | 详情 | 详情 | |
| (IVb) | 36091 | 3-(4-chlorobutyl)-1H-indole | C12H14ClN | 详情 | 详情 | |
| (IVc) | 36092 | 3-(4-bromobutyl)-1H-indole | C12H14BrN | 详情 | 详情 | |
| (IVd) | 36093 | 3-(4-iodobutyl)-1H-indole | C12H14IN | 详情 | 详情 | |
| (II) | 13002 | 4-Phenyl-1,2,3,6-tetrahydropyridine; 1,2,3,6-Tetrahydro-4-phenyl-pyridine | 10338-69-9 | C11H13N | 详情 | 详情 |