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【结 构 式】 
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【分子编号】36309 【品名】3-chloro-4-(4-chlorobutyl)-1,4-benzoxazepin-5(4H)-one 【CA登记号】 |
【 分 子 式 】C13H13Cl2NO2 【 分 子 量 】286.15716 【元素组成】C 54.57% H 4.58% Cl 24.78% N 4.89% O 11.18% |
合成路线1
该中间体在本合成路线中的序号：(IV)Alkylation of 2,3,4,5-tetrahydro-1,4-benzoxazepin-3,5-dione (I) with 1-bromo-4-chlorobutane (II) in the presence of K2CO3 afforded the 4-(chlorobutyl)benzoxazepindione (III), which was further treated with POCl3 in boiling dioxan to yield the 3-chlorobenzoxazepinone (IV). Condensation of (IV) with 4-(2-pyridyl)-1,2,5,6-tetrahydropyridine (V) using NaI and Et3N in hot DMF provided the target compound, which was isolated as the dihydrochloride salt.
| 【1】 Tatsuoka, T.; Kamei, K.; Maeda, N.; Inoue, T.; Nishimura, M.; Hirotsu, I. (Suntory Ltd.); Benzoxazepine derivs., salts thereof, and drugs containing the same. EP 0755930; WO 9624594 . |
| 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) | 36307 | 1,4-benzoxazepine-3,5(2H,4H)-dione | C9H7NO3 | 详情 | 详情 | |
| (II) | 16141 | 1-bromo-4-chlorobutane | 6940-78-9 | C4H8BrCl | 详情 | 详情 |
| (III) | 36308 | 4-(4-chlorobutyl)-1,4-benzoxazepine-3,5(2H,4H)-dione | C13H14ClNO3 | 详情 | 详情 | |
| (IV) | 36309 | 3-chloro-4-(4-chlorobutyl)-1,4-benzoxazepin-5(4H)-one | C13H13Cl2NO2 | 详情 | 详情 | |
| (V) | 36310 | 4-(2-pyridinyl)-1,2,3,6-tetrahydropyridine | C10H12N2 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(IV)In an alternative procedure, the chlorobutyl derivative (IV) was condensed with 2,4'-dipyridine (VI) by means of NaI in boiling acetone, yielding pyridinium salt (VII). Subsequent reduction of (VII) with NaBH4 in EtOH then provided the title tetrahydropyridine.
| 【1】 Tatsuoka, T.; Kamei, K.; Maeda, N.; Inoue, T.; Nishimura, M.; Hirotsu, I. (Suntory Ltd.); Benzoxazepine derivs., salts thereof, and drugs containing the same. EP 0755930; WO 9624594 . |