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【结 构 式】 
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【分子编号】21617 【品名】6-Amino-1'-[2-(1-naphthyl)ethyl]-3,4-dihydro-2H-spiro[1-benzopyran-2,4'-piperidin]-4-one 【CA登记号】 |
【 分 子 式 】C25H26N2O2 【 分 子 量 】386.49372 【元素组成】C 77.69% H 6.78% N 7.25% O 8.28% |
合成路线1
该中间体在本合成路线中的序号：(VII)Friedel-Crafts acetylation of acetaminophen (I) using acetyl chloride and AlCl3 gave acetophenone (II). Subsequent condensation of (II) with N-(tert-butoxycarbonyl)-4-piperidone (III) in the presence of pyrrolidine provided the spirochroman-2,4'-piperidine (IV), from which the diamine (V) was obtained by acid hydrolysis. The piperidine amino group of (VI) was then alkylated with 1-(2-bromoethyl)naphthalene (VI) to afford (VII). Finally, condensation of the remaining amino group of (VII) with the sulfonyl chloride (VIII) furnished the title sulfonamide.
| 【1】 Nerenberg, J.B.; et al.; 4-Oxospiro[benzopyran-2,4'-piperidines] as selective alpha1a-adrenergic receptor antagonists. Bioorg Med Chem Lett 1999, 9, 2, 291. |
| 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) | 21611 | 4'-Hydroxyacetanilide;4-Acetamidophenol;N-Acetyl-4-aminophenol;Paracetamol;Acetaminophen;p-Hydroxyacetanilide; Paracetamol; N-(4-hydroxyphenyl)acetamide | 103-90-2 | C8H9NO2 | 详情 | 详情 |
| (II) | 21612 | N-(3-acetyl-4-hydroxyphenyl)acetamide | C10H11NO3 | 详情 | 详情 | |
| (III) | 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 |
| (IV) | 21614 | 6-Aceatmido-4-oxo-3,4-dihydro-2H-spiro[1-benzopyran-2,4'-piperidin]-1'-ylcarboxylic acid tert-butyl ester | C20H26N2O5 | 详情 | 详情 | |
| (V) | 21615 | 6-Amino-3,4-dihydro-2H-spiro[1-benzopyran-2,4'-piperidin]-4-one | C13H16N2O2 | 详情 | 详情 | |
| (VI) | 21616 | 1-(2-bromoethyl)naphthalene | 13686-49-2 | C12H11Br | 详情 | 详情 |
| (VII) | 21617 | 6-Amino-1'-[2-(1-naphthyl)ethyl]-3,4-dihydro-2H-spiro[1-benzopyran-2,4'-piperidin]-4-one | C25H26N2O2 | 详情 | 详情 | |
| (VIII) | 21618 | 3,5-dimethyl-4-isoxazolesulfonyl chloride | 80466-79-1 | C5H6ClNO3S | 详情 | 详情 |