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【结 构 式】 
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【分子编号】40681 【品名】phenyl 4-(1,2,3,6-tetrahydro-4-pyridinyl)phenyl ether; 4-(4-phenoxyphenyl)-1,2,3,6-tetrahydropyridine 【CA登记号】 |
【 分 子 式 】C17H17NO 【 分 子 量 】251.32812 【元素组成】C 81.24% H 6.82% N 5.57% O 6.37% |
合成路线1
该中间体在本合成路线中的序号：(IV)Addition of the Grignard reagent prepared from 4-bromodiphenyl ether (I) to N-Boc-4-piperidone (II) gave the 4-hydroxy-4-arylpiperidine (III). Deprotection of the Boc group of (III) with concomitant dehydration of the tertiary alcohol by means of trifluoroacetic acid afforded the tetrahydropyridine (IV), which was further hydrogenated to piperidine (V) using Pd/C as the catalyst. Condensation of pieridine (V) with phenyl glycidyl ether (VI) in refluxing isopropanol yielded the desired amino alcohol, which was finally isolated as the corresponding hydrochloride salt.
| 【1】 Nakanishi, K.; Miyajima, A.; Annoura, H.; Uesugi, M.; Fukunaga, A.; Tamura, S.; Tamura-Horikawa, Y.; A novel class of Na+ and Ca2+ channel dual blockers with highly potent anti-ischemic effects. Bioorg Med Chem Lett 1999, 9, 20, 2999. |
| 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) | 35580 | 1-bromo-4-phenoxybenzene; 4-bromophenyl phenyl ether | 101-55-3 | C12H9BrO | 详情 | 详情 |
| (II) | 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 |
| (III) | 40680 | tert-butyl 4-hydroxy-4-(4-phenoxyphenyl)-1-piperidinecarboxylate | C22H27NO4 | 详情 | 详情 | |
| (IV) | 40681 | phenyl 4-(1,2,3,6-tetrahydro-4-pyridinyl)phenyl ether; 4-(4-phenoxyphenyl)-1,2,3,6-tetrahydropyridine | C17H17NO | 详情 | 详情 | |
| (V) | 40682 | phenyl 4-(4-piperidinyl)phenyl ether; 4-(4-phenoxyphenyl)piperidine | C17H19NO | 详情 | 详情 | |
| (VI) | 23932 | 2-(phenoxymethyl)oxirane; oxiranylmethyl phenyl ether | 122-60-1 | C9H10O2 | 详情 | 详情 |