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【结 构 式】 
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【药物名称】 【化学名称】1-(4-Fluorophenyl)-2-[4-(phenylsulfonyl)piperidin-1-yl]ethanone 【CA登记号】285994-99-2 【 分 子 式 】C19H20FNO3S 【 分 子 量 】361.43855 |
【开发单位】Merck Sharp & Dohme (Originator) 【药理作用】Antipsychotic Drugs, PSYCHOPHARMACOLOGIC DRUGS, 5-HT2A Antagonists |
合成路线1
The (phenylsulfanyl)piperidine (III) was obtained by condensation of N-Boc-4-piperidinol (I) with diphenyl disulfide (II) in the presence of tributylphosphine. Subsequent oxidation of sulfide (III) to the corresponding sulfone (IV) was achieved using oxone® on wet alumina. Deprotection of the N-Boc-piperidine (IV) with HCl afforded piperidine (V), which was finally alkylated with 2-bromo-4'-fluoroacetophenone (VI) to furnish the title N-phenacyl piperidine.
| 【1】 Blurton, P.; Burkamp, F.; Fletcher, S.R.; et al.; 4-(Phenylsulfonyl)piperidines: Novel, selective, and biovailable 5-HT2A receptor antagonists. J Med Chem 2002, 45, 2, 492. |
| 【2】 Macleod, A.M.; Blurton, P.; Fletcher, S.R.; Van Niel, M.B.; Burkamp, F.; Cheng, S.K.-F. (Merck Sharp & Dohme Ltd.); Phenylsulphonyl derivs. as 5-HT receptor ligands. EP 1147083; WO 0043362 . |
| 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) | 18625 | tert-butyl 4-hydroxy-1-piperidinecarboxylate | C10H19NO3 | 详情 | 详情 | |
| (II) | 17473 | diphenyl disulfide; 1-(phenyldisulfanyl)benzene; diphenyldisulfide | 882-33-7 | C12H10S2 | 详情 | 详情 |
| (III) | 32561 | tert-butyl 4-(phenylsulfanyl)-1-piperidinecarboxylate | C16H23NO2S | 详情 | 详情 | |
| (IV) | 56311 | tert-butyl 4-(phenylsulfonyl)-1-piperidinecarboxylate | C16H23NO4S | 详情 | 详情 | |
| (V) | 56312 | 4-(phenylsulfonyl)piperidine; phenyl 4-piperidinyl sulfone | C11H15NO2S | 详情 | 详情 | |
| (VI) | 27904 | 2-bromo-1-(4-fluorophenyl)-1-ethanone | 403-29-2 | C8H6BrFO | 详情 | 详情 |
Extended Information