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【结 构 式】 
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【分子编号】33453 【品名】5-methoxy-1-[4-(trifluoromethyl)phenyl]-1-pentanone O-(2-hydroxyethyl)oxime 【CA登记号】 |
【 分 子 式 】C15H20F3NO3 【 分 子 量 】319.3239496 【元素组成】C 56.42% H 6.31% F 17.85% N 4.39% O 15.03% |
合成路线1
该中间体在本合成路线中的序号：(III)Compound can be prepared in three different ways all starting from p-trifluoromethyl-5-methoxy-valerophenone (I): 1) By condensation of (I) with 2-aminooxyethylamine dihydrochloride in refluxing pyridine ethanol (C). 2) The reaction of (I) with hydroxylamine as usual yields the corresponding oxime (II), which is then condensed with 2-chloroethylamine (B) by means of KOH in DMF. 3) The reaction of the oxime (II) with Li and ethylene oxide (A) in absolute ethanol affords the O-(2-hydroxyethyl)oxime (III), which is esterified with mesyl chloride by means of triethylamine in methylene chloride giving the O-(2-mesyloxyethyl)oxime (IV). Finally, this compound is treated with NH3 in methanol at 100 C in a pressure vessel.
| 【1】 Welle, H.B.A.; Claassen, V.; Oxime ethers having anti-depressive activity. DE 2610886; FR 2304336; GB 1535226; JP 51125345; NL 7503310; US 4085225 . |
| 【2】 Thorpe, P.J.; Castaner, J.; Fluvoxamine. Drugs Fut 1978, 3, 4, 288. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (A) | 10393 | Oxirane; Ethylene oxide | 75-21-8 | C2H4O | 详情 | 详情 |
| (B) | 33455 | 2-chloro-1-ethanamine; 2-chloroethylamine | C2H6ClN | 详情 | 详情 | |
| (I) | 33451 | 5-methoxy-1-[4-(trifluoromethyl)phenyl]-1-pentanone | C13H15F3O2 | 详情 | 详情 | |
| (II) | 33452 | 5-methoxy-1-[4-(trifluoromethyl)phenyl]-1-pentanone oxime | C13H16F3NO2 | 详情 | 详情 | |
| (III) | 33453 | 5-methoxy-1-[4-(trifluoromethyl)phenyl]-1-pentanone O-(2-hydroxyethyl)oxime | C15H20F3NO3 | 详情 | 详情 | |
| (IV) | 33454 | 2-[([(E)-5-methoxy-1-[4-(trifluoromethyl)phenyl]pentylidene]amino)oxy]ethyl methanesulfonate | C16H22F3NO5S | 详情 | 详情 | |
| (C) | 21003 | 2-(aminooxy)-1-ethanamine; 2-(aminooxy)ethylamine | C2H8N2O | 详情 | 详情 |