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【结 构 式】 
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【药物名称】AM-36 【化学名称】4-[4-[2-(4-Chlorophenyl)-2-hydroxyethyl]piperazin-1-ylmethyl]-2,6-bis(tert-butyl)phenol 【CA登记号】199467-52-2, 199467-53-3 (tartrate (1:2)) 【 分 子 式 】C27H39ClN2O2 【 分 子 量 】459.07708 |
【开发单位】Amrad (Originator), DevCo (Licensee), Monash University (Codevelopment) 【药理作用】Cerebrovascular Diseases, Treatment of, NEUROLOGIC DRUGS, Stroke, Treatment of, NMDA Antagonists, Sodium Channel Blockers |
合成路线1
Alkylation of ethyl 1-piperazinecarboxylate (I) with 2-bromo-4'-chloroacetophenone (II) afforded disubstituted piperazine (III). Further cleavage of the carbamate group of (III) in refluxing HCl produced piperazine (IV). Bromide (VII) was prepared by reduction of 3,5-di-tert-butyl-4-hydroxybenzaldehyde (V) with NaBH4, followed by treatment of the resulting alcohol (VI) with PBr3. Piperazine (IV) was then condensed with bromide (VII) to give adduct (VIII). Finally, ketone reduction using LiAlH4 furnished the title alcohol.
| 【1】 Collis, M.P.; Robertson, A.D.; Kenche, V.B.; Jackson, W.R.; Jarrott, B.; Beart, P.M. (Monash University); Arylalkylpiperazine cpds. as antioxidants. JP 2000510126; WO 9743259 . |
| 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) | 24694 | N-ethoxycarbonylpiperidine; Ethyl 1-piperazinecarboxylate; N-Ethoxycarbonyl piperazine; N-Carbethoxy piperazine | 120-43-4 | C7H14N2O2 | 详情 | 详情 |
| (II) | 16720 | 2-bromo-1-(4-chlorophenyl)-1-ethanone; 2-Bromo-4'-chloroacetophenone | 536-38-9 | C8H6BrClO | 详情 | 详情 |
| (III) | 37704 | ethyl 4-[2-(4-chlorophenyl)-2-oxoethyl]-1-piperazinecarboxylate | C15H19ClN2O3 | 详情 | 详情 | |
| (IV) | 37705 | 1-(4-chlorophenyl)-2-(1-piperazinyl)-1-ethanone | C12H15ClN2O | 详情 | 详情 | |
| (V) | 14875 | 3,5-Bis(1,1-dimethylethyl)-4-hydroxybenzaldehyde; 3,5-di(tert-butyl)-4-hydroxybenzaldehyde; 3,5-Di-tert-butyl-4-hydroxybenzaldehyde | 1620-98-0 | C15H22O2 | 详情 | 详情 |
| (VI) | 37706 | 2,6-di(tert-butyl)-4-(hydroxymethyl)phenol | 88-26-6 | C15H24O2 | 详情 | 详情 |
| (VII) | 37707 | 4-(bromomethyl)-2,6-di(tert-butyl)phenol | C15H23BrO | 详情 | 详情 | |
| (VIII) | 37708 | 1-(4-chlorophenyl)-2-[4-[3,5-di(tert-butyl)-4-hydroxybenzyl]-1-piperazinyl]-1-ethanone | C27H37ClN2O2 | 详情 | 详情 |