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【结 构 式】

【分子编号】12848

【品名】1-Methyl-1,2,5,6-tetrahydro-3-pyridinecarbaldehyde

【CA登记号】

【 分 子 式 】C7H11NO

【 分 子 量 】125.17048

【元素组成】C 67.17% H 8.86% N 11.19% O 12.78%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(I)

Milameline can be obtained by three related ways: 1) By reaction of 1-methyl-1,2,3,6-tetrahydropyridine-3-carbaldehyde (I) with methoxyamine by means of triethylamine in DMF. 2) The reaction of pyridine-3-carbaldehyde (II) with methoxyamine in refluxing methanol gives the corresponding oxime (III), which is alkylated with methyl iodide in refluxing ethyl acetate yielding 3-(methoxyiminomethyl)-1-methylpyridinium iodide (IV). Finally, this compound is hydrogenated with NaBH4 in methanol/water. 3) The reaction of 1,2,3,6-tetrahydropyridine-3-carbaldehyde (V) with methoxyamine gives the corresponding oxime (VI), which is then alkylated with methyl iodide in DMF.

1 Souda, S.; Ueda, N.; Miyazawa, S.; Tagami, K.; Nomoto, S.; Okita, M.; Shimomura, N.; Kaneko, T.; Fujimoto, M.; Murakami, M.; Oketani, K.; Fujisaki, H.; Shibata, H.; Wakabayashi, T. (Eisai Co., Ltd.); Pyridine derivs., pharmaceutical compsns. comprising the same, the use of the same for the manufacture of medicaments having therapeutic or preventative value, and a process for preparing the same. AU 8781138; EP 0268956; EP 0475456; EP 0654471; EP 0786461; JP 1989006270; JP 1993247035; JP 1995291967; US 5045552; US 5998445 .
2 Graul, A.; Castaner, J.; Milameline Hydrochloride. Drugs Fut 1996, 21, 11, 1124.
3 Bergmeier, S.C.; Downs, D.A.; Moos, W.H.; Moreland, D.W.; Tecle, H. (Pfizer Inc.); O-Substd. tetrahydropyridine oxime cholinergic agents. AU 8781102; EP 0271798; JP 1988215664; US 4710508 .
4 Galliani, G.; Barzaghi, F.; Butti, A.; Bonetti, C.; Toja, E. (Aventis Pharma SA); 1,2,5,6-Tetrahydropyridine-3-carboxaldehyde oxime derivs., process for their preparation, their application as medicaments and compsns. containing them. EP 0239445; JP 1987252767; US 5219872 .
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) 12848 1-Methyl-1,2,5,6-tetrahydro-3-pyridinecarbaldehyde C7H11NO 详情 详情
(II) 12849 Nicotinaldehyde; 3-Pyridinecarboxaldehyde 500-22-1 C6H5NO 详情 详情
(III) 12850 Nicotinaldehyde O-methyloxime C7H8N2O 详情 详情
(IV) 12851 3-[(Methoxyimino)methyl]-1-methylpyridinium iodide C8H11IN2O 详情 详情
(V) 12852 1,2,5,6-Tetrahydro-3-pyridinecarbaldehyde C6H9NO 详情 详情
(VI) 12853 1,2,5,6-Tetrahydro-3-pyridinecarbaldehyde O-methyloxime C7H12N2O 详情 详情
Extended Information