【结 构 式】 |
【分子编号】40738 【品名】1-[2,5-bis(2,2,2-trifluoroethoxy)phenyl]-1-ethanone 【CA登记号】76784-40-2 |
【 分 子 式 】C12H10F6O3 【 分 子 量 】316.2000192 【元素组成】C 45.58% H 3.19% F 36.05% O 15.18% |
合成路线1
该中间体在本合成路线中的序号:(IV)The etherification of hydroquinone (I) with 2,2,2-trifluoroethyl trifluoromethanesulfonate (II) by means of K2CO3 in refluxing acetone gives the corresponding diether (III), which is submitted to a Friedel-Crafts condensation with Ac-Cl or Ac2O and AlCl3 in dichloromethane yielding the acetophenone (IV). The chlorination of (IV) with Cl2 in acetic acid at 55 C gives the alpha, alpha-dichloroacetophenone (V), which is further chlorinated with Cl2 and NaOAc in acetic acid at 100 C affording the corresponding trichloro derivative (VI). The reaction of (VI) with 2-(aminomethyl)pyridine (VII) in cyclohexane/toluene or isopropanol furnishes the benzamide (VIII), which is finally hydrogenated with H2 over Pt/C in isopropanol/acetic acid to give the target piperidine derivative.
【1】 Leir, C.M. (3M Pharmaceuticals); Process for the preparation of derivs. of pyrrolidine and piperidine. US 4642384 . |
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) | 13163 | p-Dihydrobenzene; Hydroquinone | 123-31-9 | C6H6O2 | 详情 | 详情 |
(II) | 40675 | 2,2,2-trifluoroethyl trifluoromethanesulfonate | 6226-25-1 | C3H2F6O3S | 详情 | 详情 |
(III) | 40737 | 1,4-bis(2,2,2-trifluoroethoxy)benzene; 4-(2,2,2-trifluoroethoxy)phenyl 2,2,2-trifluoroethyl ether | 66300-61-6 | C10H8F6O2 | 详情 | 详情 |
(IV) | 40738 | 1-[2,5-bis(2,2,2-trifluoroethoxy)phenyl]-1-ethanone | 76784-40-2 | C12H10F6O3 | 详情 | 详情 |
(V) | 40739 | 1-[2,5-bis(2,2,2-trifluoroethoxy)phenyl]-2,2-dichloro-1-ethanone | C12H8Cl2F6O3 | 详情 | 详情 | |
(VI) | 40740 | 1-[2,5-bis(2,2,2-trifluoroethoxy)phenyl]-2,2,2-trichloro-1-ethanone | 76784-42-4 | C12H7Cl3F6O3 | 详情 | 详情 |
(VII) | 13582 | 2-Pyridinylmethanamine; 2-Pyridinylmethylamine; 2-(Aminomethyl)pyridine | 3731-51-9 | C6H8N2 | 详情 | 详情 |
(VIII) | 33970 | N-(2-pyridinylmethyl)-2,5-bis(2,2,2-trifluoroethoxy)benzamide | C17H14F6N2O3 | 详情 | 详情 | |
(IX) | 18983 | 1,4-dibromobenzene | 106-37-6 | C6H4Br2 | 详情 | 详情 |
(X) | 19483 | 2,2,2-trifluoro-1-ethanol | 75-89-8 | C2H3F3O | 详情 | 详情 |