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【结 构 式】 
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【分子编号】31689 【品名】4-Benzyloxyphenacyl chloride; 1-[4-(Benzyloxy)phenyl]-2-chloro-1-ethanone 【CA登记号】39188-62-0 |
【 分 子 式 】C15H13ClO2 【 分 子 量 】260.71972 【元素组成】C 69.1% H 5.03% Cl 13.6% O 12.27% |
与该中间体有关的原料药合成路线共 3 条
合成路线1
该中间体在本合成路线中的序号：(XV)The condensation of 4-benzyloxyphenacyl chloride (XV) with the amine (IV) in refluxing CH2Cl2 gives N-(3,4-dimethoxyphenylethyl)-4-benzyloxyphenacylamine (XVI), which is reduced with NaSH4 in ethanol, also affording the protected product (VI).
| 【1】 Ikezaki, M.; Ito, N.; Okazaki, Y.; Hoshiyama, M.; Nagao, T. (Tanabe Seiyaku Co., Ltd.); Benzyl alcohol, amine derivatives. AT 343628B; BE 0833731; DE 2542881; FR 2326182; GB 1499345; JP 50157327; JP 53010974; JP 7795620; JP 7795621; NL 7511564; US 4032575; US 4072759 . |
| 【2】 Blancafort, P.; Castaner, J.; Serradell, M.N.; TA-064. Drugs Fut 1982, 7, 6, 407. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (IV) | 10098 | 2-(3,4-Dimethoxyphenyl)-1-ethanamine; 3,4-Dimethoxyphenethylamine; 2-(3,4-Dimethoxyphenyl)ethylamine | 120-20-7 | C10H15NO2 | 详情 | 详情 |
| (VI) | 31687 | (1R)-1-[4-(benzyloxy)phenyl]-2-[(3,4-dimethoxyphenethyl)amino]-1-ethanol | C25H29NO4 | 详情 | 详情 | |
| (XV) | 31689 | 4-Benzyloxyphenacyl chloride; 1-[4-(Benzyloxy)phenyl]-2-chloro-1-ethanone | 39188-62-0 | C15H13ClO2 | 详情 | 详情 |
| (XVI) | 10100 | 1-[4-(Benzyloxy)phenyl]-2-[(3,4-dimethoxyphenethyl)amino]-1-ethanone; N-(3,4-Dimethoxyphenylethyl)-4-benzyloxyphenacylamine | C25H27NO4 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(XV)The oxidation of 4-benzyloxyphenacyl chloride (XV) with KI and DMSO gives 4-benzyloxy-alpha-oxophenylacetaldehyde (XVII), which is condensed with the amine (IV) to afford the corresponding Schiff base (XVIII). Finally, this compound is reduced with NaBH4 yielding the protected product (VI), already obtained.
| 【1】 Ikezaki, M.; Umino, N.; Iwakuma, T.; Process for preparation of benzyl alcohol derivatives. JP 52051334 . |
| 【2】 Ikezaki, M.; Umino, N.; Iwakuma, T.; Process for preparation of benzyl alcohol derivatives. JP 52051335 . |
| 【3】 Blancafort, P.; Castaner, J.; Serradell, M.N.; TA-064. Drugs Fut 1982, 7, 6, 407. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (IV) | 10098 | 2-(3,4-Dimethoxyphenyl)-1-ethanamine; 3,4-Dimethoxyphenethylamine; 2-(3,4-Dimethoxyphenyl)ethylamine | 120-20-7 | C10H15NO2 | 详情 | 详情 |
| (VI) | 31687 | (1R)-1-[4-(benzyloxy)phenyl]-2-[(3,4-dimethoxyphenethyl)amino]-1-ethanol | C25H29NO4 | 详情 | 详情 | |
| (XV) | 31689 | 4-Benzyloxyphenacyl chloride; 1-[4-(Benzyloxy)phenyl]-2-chloro-1-ethanone | 39188-62-0 | C15H13ClO2 | 详情 | 详情 |
| (XVII) | 31696 | 2-[4-(benzyloxy)phenyl]-2-oxoacetaldehyde; 4-benzyloxy-alpha-oxophenylacetaldehyde | C15H12O3 | 详情 | 详情 | |
| (XVIII) | 31697 | 1-[4-(benzyloxy)phenyl]-2-[(3,4-dimethoxyphenethyl)imino]-1-ethanone | C25H25NO4 | 详情 | 详情 |
合成路线3
该中间体在本合成路线中的序号：(I)
| 【1】 Gharpure MM. 2006．Process for preparation of galanthamine. W0 2006072818[本专利为Emcure Pharmaceuticals Ltd. (IN)所有] |
| 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) | 31689 | 4-Benzyloxyphenacyl chloride; 1-[4-(Benzyloxy)phenyl]-2-chloro-1-ethanone | 39188-62-0 | C15H13ClO2 | 详情 | 详情 |
| (II) | 66407 | 2-(4-(benzyloxy)phenyl)-N-methylacetamide | C16H17NO2 | 详情 | 详情 | |
| (III) | 66408 | 2-(4-(benzyloxy)phenyl)-N-methylethanamine | 38961-21-6 | C16H19NO | 详情 | 详情 |
| (IV) | 66409 | 5-(benzyloxy)-N-(4-(benzyloxy)phenethyl)-2-bromo-4-methoxy-N-methylbenzamide | C31H30BrNO4 | 详情 | 详情 | |
| (V) | 66410 | 2-bromo-5-hydroxy-N-(4-hydroxyphenethyl)-4-methoxy-N-methylbenzamide | C17H18BrNO4 | 详情 | 详情 | |
| (VI) | 66411 | 1-bromo-11-methyl-10,11-dihydro-4aH-benzo[2,3]benzofuro[4,3-cd]azepine-6,12(5H,9H)-dione | C16H14BrNO3 | 详情 | 详情 | |
| (VII) | 66412 | 1-bromo-6-hydroxy-11-methyl-5,6,10,11-tetrahydro-4aH-benzo[2,3]benzofuro[4,3-cd]azepin-12(9H)-one | C16H16BrNO3 | 详情 | 详情 | |
| (VIII) | 66413 | 11-methyl-5,6,9,10,11,12-hexahydro-4aH-benzo[2,3]benzofuro[4,3-cd]azepin-6-ol | C16H19NO2 | 详情 | 详情 |
Extended Information