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【结 构 式】 
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【分子编号】41592 【品名】2-(6,7-dimethyl-1-oxo-1,2,3,4-tetrahydro-2-naphthalenyl)acetonitrile 【CA登记号】 |
【 分 子 式 】C14H15NO 【 分 子 量 】213.27924 【元素组成】C 78.84% H 7.09% N 6.57% O 7.5% |
合成路线1
该中间体在本合成路线中的序号：(IV)Mannich reaction of 6,7-dimethyltetralone (I) with dimethylamine and formaldehyde provided amino ketone (II). Subsequent quaternization of (II) with MeI in acetone gave ammonium salt (III), that was further displaced by KCN yielding nitrile (IV). Acidic hydrolysis of the cyano group of (IV) produced carboxylic acid (V). This was then coupled with pyrrolidine (VI) employing BOP reagent to furnish amide (VII). Reduction of the ketone and amide functions of (VII) by means of vitride?in toluene afforded amino alcohol (VIII). After alcohol (VIII) dehydration with ethanolic HCl, the title compound was isolated as the fumarate salt.
| 【1】 Kai, N.; Kanehira, A.; Morie, T.; Hino, K.; Kawashima, K.; Shimizu, I.; Akiyama, K. (Dainippon Pharmaceutical Co., Ltd.); 1-[omega-(3,4-Dihydro-2-naphthalenyl)alkyl]cyclic amine derivs., process for producing the same, and medicinal compsn. containing the same. EP 0825180; US 5847159; WO 9633169 . |
| 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) | 41589 | 6,7-dimethyl-3,4-dihydro-1(2H)-naphthalenone | C12H14O | 详情 | 详情 | |
| (II) | 41590 | 2-[(dimethylamino)methyl]-6,7-dimethyl-3,4-dihydro-1(2H)-naphthalenone | C15H21NO | 详情 | 详情 | |
| (III) | 41591 | (6,7-dimethyl-1-oxo-1,2,3,4-tetrahydro-2-naphthalenyl)-N,N,N-trimethylmethanaminium iodide | C16H24INO | 详情 | 详情 | |
| (IV) | 41592 | 2-(6,7-dimethyl-1-oxo-1,2,3,4-tetrahydro-2-naphthalenyl)acetonitrile | C14H15NO | 详情 | 详情 | |
| (V) | 41593 | 2-(6,7-dimethyl-1-oxo-1,2,3,4-tetrahydro-2-naphthalenyl)acetic acid | C14H16O3 | 详情 | 详情 | |
| (VI) | 11376 | Pyrrolidine | 123-75-1 | C4H9N | 详情 | 详情 |
| (VII) | 41594 | 6,7-dimethyl-2-[2-oxo-2-(1-pyrrolidinyl)ethyl]-3,4-dihydro-1(2H)-naphthalenone | C18H23NO2 | 详情 | 详情 | |
| (VIII) | 41595 | 6,7-dimethyl-2-[2-(1-pyrrolidinyl)ethyl]-1,2,3,4-tetrahydro-1-naphthalenol | C18H27NO | 详情 | 详情 |