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【结 构 式】 
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【分子编号】44646 【品名】2-(4-methyl-2-phenyl-1-piperazinyl)nicotinic acid 【CA登记号】 |
【 分 子 式 】C17H19N3O2 【 分 子 量 】297.35688 【元素组成】C 68.67% H 6.44% N 14.13% O 10.76% |
合成路线1
该中间体在本合成路线中的序号：(VI)2) [14C]-Labeled: The condensation of 2-chloro-3-nitropyridine (I) with 1-methyl-3-phenylpiperazine (II) by means of KF at 140 C in DMF gives 4-methyl-1-(3-nitropyridin-2-yl)-2-phenylpiperazine (III), which is reduced with H2 over Pd/C in ethanol to the amine (IV). The reaction of (IV) with pentyl nitrite and bromoform at 100 C yields 1-(3-bromopyridin-2-yl)-4-methyl-2-phenylpiperazine (V), which by reaction with butyllithium and [14C]-labeled CO2 in ether is converted into 2-(4-methyl-2-phenylpiperazin-1-yl)pyridine-3-carboxylic acid (VI). The reduction of (VI) with LiAlH4 in hot THF affords the corresponding alcohol (VII), which is finally cyclized in hot H2SO4.
| 【1】 Wieringa, J.H.; Kaspersen, F.M.; van Rooij, F.A.M.; Sperling, E.G.M.; The synthesis of ORG 3770 labelled with 3H, 13C and 14C. J Label Compd Radiopharm 1989, 27, 9, 1055. |
| 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) | 10321 | 2-Chloro-3-nitropyridine | 5470-18-8 | C5H3ClN2O2 | 详情 | 详情 |
| (II) | 10322 | 1-Methyl-3-phenylpiperazine | 5271-27-2 | C11H16N2 | 详情 | 详情 |
| (III) | 10323 | 4-Methyl-1-(3-nitro-2-pyridinyl)-2-phenylpiperazine | C16H18N4O2 | 详情 | 详情 | |
| (IV) | 10324 | 2-(4-Methyl-2-phenylpiperazino)-3-pyridinamine; 2-(4-Methyl-2-phenylpiperazino)-3-pyridinylamine | C16H20N4 | 详情 | 详情 | |
| (V) | 10325 | 1-(3-Bromo-2-pyridinyl)-4-methyl-2-phenylpiperazine | C16H18BrN3 | 详情 | 详情 | |
| (VI) | 10326 | 2-(4-Methyl-2-phenylpiperazino)nicotinic acid | C17H19N3O2 | 详情 | 详情 | |
| (VI) | 44646 | 2-(4-methyl-2-phenyl-1-piperazinyl)nicotinic acid | C17H19N3O2 | 详情 | 详情 | |
| (VII) | 10320 | [2-(4-Methyl-2-phenylpiperazino)-3-pyridinyl]methanol | 61337-89-1 | C17H21N3O | 详情 | 详情 |
| (VII) | 44647 | [2-(4-methyl-2-phenyl-1-piperazinyl)-3-pyridinyl]methanol | C17H21N3O | 详情 | 详情 |