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【结 构 式】 
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【分子编号】51418 【品名】3-[1-(3,5-dimethoxybenzyl)-4-piperidinyl]-6-fluoro-1,2-benzisoxazole; 3-[[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]methyl]-5-methoxyphenyl methyl ether 【CA登记号】 |
【 分 子 式 】C21H23FN2O3 【 分 子 量 】370.4237032 【元素组成】C 68.09% H 6.26% F 5.13% N 7.56% O 12.96% |
合成路线1
该中间体在本合成路线中的序号：(IV)The condensation of 3,5-dimethoxybenzoic acid (I) with 4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidine (II) by means of DCC and HOBT in DMF gives the piperidide (III), which is reduced with LiAlH4 in THF to yield 1-(3,5-dimethoxybenzyl)-4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidine (IV). The reduction of (IV) with Li in liquid ammonia affords the 1,4-dihydro derivative (V), which is finally cyclized with phenylhydrazine (VI) in refluxing aqueous sulfuric acid to provide the target tetrahydrocarbazolone.
| 【1】 Masaguer, C.F.; Loza, M.I.; Fontenla, J.A.; Brea, J.; Raviña, E.; Tristan, H.; Butyrophenone analogues in the carbazole series as potential atypical antipsychotics: Synthesis and determination of affinities at D2, 5-HT2A, 5-HT2B and 5-HT2C receptors. Eur J Med Chem 2000, 35, 1, 83. |
| 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) | 22761 | 3,5-dimethoxybenzoic acid | 1132-21-4 | C9H10O4 | 详情 | 详情 |
| (II) | 17910 | 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole | C12H13FN2O | 详情 | 详情 | |
| (III) | 51420 | (3,5-dimethoxyphenyl)[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]methanone | C21H21FN2O4 | 详情 | 详情 | |
| (IV) | 51418 | 3-[1-(3,5-dimethoxybenzyl)-4-piperidinyl]-6-fluoro-1,2-benzisoxazole; 3-[[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]methyl]-5-methoxyphenyl methyl ether | C21H23FN2O3 | 详情 | 详情 | |
| (V) | 51419 | 3-[[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]methyl]-5-methoxy-1,4-cyclohexadien-1-yl methyl ether; 3-[1-[(3,5-dimethoxy-2,5-cyclohexadien-1-yl)methyl]-4-piperidinyl]-6-fluoro-1,2-benzisoxazole | C21H25FN2O3 | 详情 | 详情 | |
| (VI) | 11818 | Phenyl hydrazine; 1-Phenylhydrazine | 100-63-0 | C6H8N2 | 详情 | 详情 |