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【结 构 式】 
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【分子编号】26419 【品名】1-(4-aminophenyl)-2-(1-benzyl-4-piperidinyl)-1-ethanone 【CA登记号】 |
【 分 子 式 】C20H24N2O 【 分 子 量 】308.42344 【元素组成】C 77.89% H 7.84% N 9.08% O 5.19% |
合成路线1
该中间体在本合成路线中的序号：(VII)The condensation of 1-benzylpiperidin-4-one (I) with 4-acetamidoacetophenone (II) by means of lithium diisopropylamide in HMPA/THF gives the piperidinol (III), which is dehydrated by reaction first with SOCl2 and then with NaOH yielding a mixture of compounds (IV) and (V) with exo and endo double bonds. This mixture is hydrogenated with H2 over PtO2 in ethanol/toluene to afford the saturated piperidine derivative (VI), which is treated with HCl in refluxing ethanol to cleave the acetamido substituent giving (VII) with a free amino group. Finally, this compound is condensed with 4-chloro-5-methylpyrimidine (VIII) by means of HCl in refluxing ethanol/CHCl3.
| 【1】 Kimura, T.; Kuroki, Y.; Fujiwara, H.; Anpeiji, S. (Ube Industries, Ltd.); Pyrimidine cpd.. EP 0664291; WO 9407890 . |
| 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) | 15720 | 1-benzyltetrahydro-4(1H)-pyridinone; 1-Benzyl-4-piperidone; N-Benzyl-4-piperidone; 1-(benzyl)-4-piperidinone; 1-benzylpiperidin-4-one; 1-(benzyl)piperidin-4-one | 3612-20-2 | C12H15NO | 详情 | 详情 |
| (II) | 26414 | N-(4-acetylphenyl)acetamide | 2719-21-3 | C10H11NO2 | 详情 | 详情 |
| (III) | 26415 | N-[4-[2-(1-benzyl-4-hydroxy-4-piperidinyl)acetyl]phenyl]acetamide | C22H26N2O3 | 详情 | 详情 | |
| (IV) | 26416 | N-[4-[2-(1-benzyl-4-piperidinylidene)acetyl]phenyl]acetamide | C22H24N2O2 | 详情 | 详情 | |
| (V) | 26417 | N-[4-[2-(1-benzyl-1,2,3,6-tetrahydro-4-pyridinyl)acetyl]phenyl]acetamide | C22H24N2O2 | 详情 | 详情 | |
| (VI) | 26418 | N-[4-[2-(1-benzyl-4-piperidinyl)acetyl]phenyl]acetamide | C22H26N2O2 | 详情 | 详情 | |
| (VII) | 26419 | 1-(4-aminophenyl)-2-(1-benzyl-4-piperidinyl)-1-ethanone | C20H24N2O | 详情 | 详情 | |
| (VIII) | 26420 | 4-chloro-5-methylpyrimidine | C5H5ClN2 | 详情 | 详情 |