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【结 构 式】 
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【分子编号】13437 【品名】2-[4-(Aminomethyl)phenoxy]-N,N-dimethyl-1-ethanamine; N-[2-[4-(Aminomethyl)phenoxy]ethyl]-N,N-dimethylamine 【CA登记号】 |
【 分 子 式 】C11H18N2O 【 分 子 量 】194.2768 【元素组成】C 68.01% H 9.34% N 14.42% O 8.24% |
合成路线1
该中间体在本合成路线中的序号：(V)The condensation of 4-hydroxybenzaldehyde (I) with 2-(dimethylamino)ethyl chloride (II) by means of K2CO3 in hot isopropyl ether yields 4-[2-(dimethylamino)ethoxy]benzaldehyde (III), which is treated with hydroxylamine hydrochloride in refluxing ethanol to afford the corresponding oxime (IV). The hydrogenation of (IV) with H2 over RaNi in methanolic ammonia yields 4-[2-(dimethylamino)ethoxy]benzylamine (V), which is finally condensed with 3,4-dimethoxybenzoyl chloride (VI) (obtain303ed from the corresponding acid (VII) with SOCl2) in toluene.
| 【1】 Castaner, J.; Mealy, N.; Itopride Hydrochloride. Drugs Fut 1995, 20, 12, 1220. |
| 【2】 Ogawa, N.; Yasuda, S.; Kato, H.; Sakaguchi, J.; Iwanaga, Y.; Ito, Y.; Nishino, H.; Synthesis, gastrointestinal prokinetic activity and structure-activity relationships of novel N-[[2-(dialkylamino)ethoxy]benzyl]benzamide derivatives. Chem Pharm Bull 1992, 40, 1, 202-11. |
| 【3】 Itoh, Y.; Kato, H.; Koshinaka, E.; Ogawa, N.; Nishino, H.; Sakaguchi, J. (Hokuriku Seiyaku Co., Ltd.); Amide cpds., process for preparing the same, and compsn. for activating gastric motor function containing the same. AU 8821862; EP 0306827; JP 1989066153; JP 1989079144; JP 1989085960; JP 1989093568; US 4983633 . |
| 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) | 13433 | 4-Hydroxybenzaldehyde; p-Hydroxybenzaldehyde | 123-08-0 | C7H6O2 | 详情 | 详情 |
| (II) | 11907 | Dimethylaminoethyl chloride; 2-Dimethylaminoethyl chloride; 2-Chloro-N,N-dimethyl-1-ethanamine; N-(2-Chloroethyl)-N,N-dimethylamine | 107-99-3 | C4H10ClN | 详情 | 详情 |
| (III) | 13435 | 4-[2-(Dimethylamino)ethoxy]benzaldehyde | C11H15NO2 | 详情 | 详情 | |
| (IV) | 13436 | 4-[2-(Dimethylamino)ethoxy]benzaldehyde oxime | C11H16N2O2 | 详情 | 详情 | |
| (V) | 13437 | 2-[4-(Aminomethyl)phenoxy]-N,N-dimethyl-1-ethanamine; N-[2-[4-(Aminomethyl)phenoxy]ethyl]-N,N-dimethylamine | C11H18N2O | 详情 | 详情 | |
| (VI) | 13438 | 3,4-Dimethoxybenzoyl chloride | 3535-37-3 | C9H9ClO3 | 详情 | 详情 |
| (VII) | 13439 | 3,4-Dimethoxybenzoic acid | 93-07-2 | C9H10O4 | 详情 | 详情 |