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【结 构 式】 
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【药物名称】Dabelotine mesilate, S-12024-2 【化学名称】(±)-1-Methyl-8-(morpholin-2-ylmethoxy)-1,2,3,4-tetrahydroquinoline methanesulfonate 【CA登记号】153049-48-0, 118976-38-8 (free base) 【 分 子 式 】C16H26N2O5S 【 分 子 量 】358.46002 |
【开发单位】ADIR (Originator), Servier (Originator) 【药理作用】Cognition Disorders, Treatment of, NEUROLOGIC DRUGS |
合成路线1
The condensation of 4-benzyl-2-(chloromethyl)morpholine (I) with 8-hydroxy-1,2,3,4-tetrahydroquinoline (II) by means of NaH in hot DMF gives 8-(4-benzylmorpholin-2-ylmethoxy)-1,2,3,4-tetrahydroquinoline (III), which is methylated with methyl iodide and K2CO3 in refluxing acetone yielding the corresponding N-methyl derivative (IV). Finally, this compound is debenzylated by hydrogenolysis with H2 over Pd/C in ethanol.
| 【1】 Tracy, M.; Ngo, J.; Castaner, J.; Dabelotine Mesylate. Drugs Fut 1996, 21, 9, 890. |
| 【2】 Regnier, G.; Guillonneau, C.; Lepagnol, J. (ADIR et Cie.); Novel morpholine derivs., process for their preparation and pharmaceutical compsns. containing them. AU 8813520; EP 0286495; FR 2612926; JP 1988255279; US 4782054 . |
| 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) | 13396 | 4-Benzyl-2-(chloromethyl)morpholine | C12H16ClNO | 详情 | 详情 | |
| (II) | 16022 | 1,2,3,4-tetrahydro-8-quinolinol | C9H11NO | 详情 | 详情 | |
| (III) | 16023 | (4-benzyl-1,4-oxazinan-2-yl)methyl 1,2,3,4-tetrahydro-8-quinolinyl ether; 8-[(4-benzyl-1,4-oxazinan-2-yl)methoxy]-1,2,3,4-tetrahydroquinoline | C21H26N2O2 | 详情 | 详情 | |
| (IV) | 16024 | 8-[(4-benzyl-1,4-oxazinan-2-yl)methoxy]-1-methyl-1,2,3,4-tetrahydroquinoline; (4-benzyl-1,4-oxazinan-2-yl)methyl 1-methyl-1,2,3,4-tetrahydro-8-quinolinyl ether | C22H28N2O2 | 详情 | 详情 |
Extended Information