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【结 构 式】 
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【药物名称】AC-165024 【化学名称】N-Cyclooctyl-N-[1-[3-(4-fluorophenoxy)propyl]piperidin-4-yl]propanamide 【CA登记号】319428-14-3 【 分 子 式 】C25H39FN2O2 【 分 子 量 】418.60018 |
【开发单位】ACADIA (Originator) 【药理作用】Antipsychotic Drugs, PSYCHOPHARMACOLOGIC DRUGS, 5-HT2A Antagonists, 5-HT2A Inverse Agonists |
合成路线1
The reductive alkylation of cyclooctylamine (II) with N-Boc-4-piperidinone (I) in the presence of sodium cyanoborohydride afforded the secondary amine (III), which was condensed with propionyl chloride, yielding amide (IV). Deprotection of the Boc group of (IV) by means of HCl in dioxan provided piperidine (V). This was finally alkylated with 1-(3-chloropropoxy)-4-fluorobenzene (VI) to furnish the title compound.
| 【1】 Hansen, H.C.; et al.; Multistep solution-phase parallel synthesis of spiperone analogues. Bioorg Med Chem Lett 2000, 10, 21, 2435. |
| 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) | 18620 | tert-butyl 4-oxo-1-piperidinecarboxylate;BOC-Piperidone;N-(tert-Butoxycarbonyl)-4-piperidone; N-Boc-4-piperidone | 79099-07-3 | C10H17NO3 | 详情 | 详情 |
| (II) | 22152 | cyclooctanamine; cyclooctylamine | 5452-37-9 | C8H17N | 详情 | 详情 |
| (III) | 46524 | tert-butyl 4-(cyclooctylamino)-1-piperidinecarboxylate | C18H34N2O2 | 详情 | 详情 | |
| (IV) | 46525 | tert-butyl 4-[cyclooctyl(propionyl)amino]-1-piperidinecarboxylate | C21H38N2O3 | 详情 | 详情 | |
| (V) | 46526 | N-cyclooctyl-N-(4-piperidinyl)propanamide | C16H30N2O | 详情 | 详情 | |
| (VI) | 30524 | 3-chloropropyl 4-fluorophenyl ether; 1-(3-chloropropoxy)-4-fluorobenzene; 1-(4-Fluorophenoxy)-3-chloropropane | 1716-42-3 | C9H10ClFO | 详情 | 详情 |
Extended Information