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【结 构 式】 
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【药物名称】SL-88.0338 【化学名称】2-[1-(3-Ethoxybenzoyl)piperidin-4-ylmethyl]-5,8-dimethoxy-1,2,3,4-tetrahydroisoquinoline 【CA登记号】214693-17-1 【 分 子 式 】C26H34N2O4 【 分 子 量 】438.57188 |
【开发单位】Sanofi-synthélabo (Originator) 【药理作用】Anxiolytics, PSYCHOPHARMACOLOGIC DRUGS, 5-HT1A Antagonists |
合成路线1
Reduction of ethyl 4-piperidinecarboxylate (I) with LiAlH4 in THF provided 4-piperidinemethanol (II), which was coupled with 3-ethoxybenzoyl chloride (III) in the presence of Et3N, yielding amide (IV). Subsequent treatment of (IV) with p-toluenesulfonyl chloride in pyridine afforded the corresponding tosylate (V. This was finally condensed with 5,8-dimethoxy-1,2,3,4-tetrahydroisoquinoline (VI) to furnish the title compound.
| 【1】 George, P.; Sevrin, M.; Maloizel, C.; Tixidre, A.; Froissant, J. (Sanofi-Synthelabo ); Derivs. of 2-[(4-piperidinyl)methyl]-1,2,3, 4-tetrahydroisoquinoline, their use in therapy. AU 8929617; EP 0351255; JP 1990025481; US 4925850 . |
| 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) | 17410 | Ethyl isonipecotate; ethyl 4-piperidinecarboxylate | 1126-09-6 | C8H15NO2 | 详情 | 详情 |
| (II) | 32954 | 4-piperidinylmethanol | C6H13NO | 详情 | 详情 | |
| (III) | 32955 | 3-ethoxybenzoyl chloride | 61956-65-8 | C9H9ClO2 | 详情 | 详情 |
| (IV) | 32956 | (3-ethoxyphenyl)[4-(hydroxymethyl)-1-piperidinyl]methanone | C15H21NO3 | 详情 | 详情 | |
| (V) | 32957 | [1-(3-ethoxybenzoyl)-4-piperidinyl]methyl 4-methylbenzenesulfonate | C22H27NO5S | 详情 | 详情 | |
| (VI) | 32958 | 5,8-dimethoxy-1,2,3,4-tetrahydroisoquinoline; 5-methoxy-1,2,3,4-tetrahydro-8-isoquinolinyl methyl ether | C11H15NO2 | 详情 | 详情 |
Extended Information