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【结 构 式】 
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【分子编号】56248 【品名】N,N-diethyl-4-[hydroxy(3-methoxyphenyl)methyl]benzamide 【CA登记号】 |
【 分 子 式 】C19H23NO3 【 分 子 量 】313.39656 【元素组成】C 72.82% H 7.4% N 4.47% O 15.32% |
与该中间体有关的原料药合成路线共 1 条
合成路线1
该中间体在本合成路线中的序号：(VI)Friedel-Crafts acylation of toluene (II) with 3-methoxybenzoyl chloride (I) gave benzophenone (III). Subsequent methyl group oxidation using KMnO4 afforded carboxylic acid (IV), which was further converted to amide (V) by activation with SOCl2, followed by treatment with diethylamine. Reduction of the keto group of (V) by means of NaBH4 yielded alcohol (VI). The required benzhydryl chloride (VII) was then prepared by treatment of alcohol (VI) with concentrated HCl.
| 【1】 Evans, S.M.; Lenz, G.R.; Probes of receptor mediated phenomena 19. Synthesis of (+)-4-[(alphaR)-alpha((2S,5R)-4-allyl-2,5-dimethyl-1-piperazinyl)-3-methoxybenzyl]-N,N-diethylbenzamide (SNC 80): A highly selective, nonpeptide delta opioid receptor agonist. Chemtracts - Org Chem 1994, 7, 6, 395. |
| 【2】 Calderon, S.N.; et al.; Probes for narcotic receptor mediated phenomena: 23. Synthesis, opioid receptor binding, and bioassay of the highly selective delta agonist (+)-4-[(alphaR)-alpha-((2S,5R)-4-allyl-2, 5-dimethyl-1-piperazinyl)-3-methoxybenzyl]-N, N-diethylbenzamide (SNC 80). J Med Chem 1997, 40, 5, 695. |
| 【3】 Calderon, S.N.; et al.; Probes for narcotic receptor mediated phenomena. 19. Synthesis of (+)-4-[(alphaR)-alpha-((2S,5R)-4-allyl-2, 5-dimethyl-1-piperazinyl)-3-methoxybenzyl]-N, N-diethylbenzamide (SNC 80): A highly selective, nonpeptide delta opioid receptor agonist. J Med Chem 1994, 14, 37, 2125. |
| 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) | 16760 | 3-methoxybenzoyl chloride | 1711-05-3 | C8H7ClO2 | 详情 | 详情 |
| (II) | 12890 | Toluene | 108-88-3 | C7H8 | 详情 | 详情 |
| (III) | 56245 | (3-methoxyphenyl)(4-methylphenyl)methanone | C15H14O2 | 详情 | 详情 | |
| (IV) | 56246 | 4-(3-methoxybenzoyl)benzoic acid | C15H12O4 | 详情 | 详情 | |
| (V) | 56247 | N,N-diethyl-4-(3-methoxybenzoyl)benzamide | C19H21NO3 | 详情 | 详情 | |
| (VI) | 56248 | N,N-diethyl-4-[hydroxy(3-methoxyphenyl)methyl]benzamide | C19H23NO3 | 详情 | 详情 | |
| (VII) | 56249 | 4-[chloro(3-methoxyphenyl)methyl]-N,N-diethylbenzamide | C19H22ClNO2 | 详情 | 详情 |
Extended Information