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【结 构 式】 
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【分子编号】33887 【品名】N-[1-benzyl-4-(methoxymethyl)-4-piperidinyl]-N-phenylamine; 1-benzyl-4-(methoxymethyl)-N-phenyl-4-piperidinamine 【CA登记号】 |
【 分 子 式 】C20H26N2O 【 分 子 量 】310.43932 【元素组成】C 77.38% H 8.44% N 9.02% O 5.15% |
合成路线1
该中间体在本合成路线中的序号：(IV)The esterification of 1-benzyl-4-(phenylamino)piperidine-4-carboxylic acid (I) with ethanol and H2SO4 gives the corresponding ethyl ester (II), which is reduced with LiAlH2(OCH2CH2OCH3)2 in benzene affording 1-benzyl-4-(phenylamino)piperidine-4-methanol (III) The methylation of (III) with methyl iodide and NaH in HMPA yields 1-benzyl-4-methoxymethyl-4-(phenylamino)piperidine (IV), which is refluxed with propionic anhydride (A) to give N-[4-(methoxymethyl)-1-benzyl-4-piperidyl]propionanilide (V). The hydrogenolysis of (V) with H2 over Raney-Ni in methanol yields N-[4-(methoxymethyl)-4-piperidyl]propionanilide (VI), which is finally condensed with 2-thiopheneethanol methanesulfonate (B) by means of Na2CO3 in methyl isobutyl ketone.
| 【1】 Van Daele, P.G.H.; et al.; Synthetic analgesics: N-(1-[2-arylethyl]-4-substituted-4-piperidinyl)-N-arylalkanamides. Arzneim-Forsch Drug Res 1976, 26, 8, 1521. |
| 【2】 Castaner, J.; Arrigoni-Martelli, E.; Sufentanil. Drugs Fut 1977, 2, 5, 334. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (A) | 20095 | propionic anhydride | 123-62-6 | C6H10O3 | 详情 | 详情 |
| (B) | 33889 | 2-(2-thienyl)-1-ethanol; Thiophene-2-ethanol | 5402-55-1 | C6H8OS | 详情 | 详情 |
| (I) | 33884 | 4-anilino-1-benzyl-4-piperidinecarboxylic acid | C19H22N2O2 | 详情 | 详情 | |
| (II) | 33885 | ethyl 4-anilino-1-benzyl-4-piperidinecarboxylate | C21H26N2O2 | 详情 | 详情 | |
| (III) | 33886 | (4-anilino-1-benzyl-4-piperidinyl)methanol | C19H24N2O | 详情 | 详情 | |
| (IV) | 33887 | N-[1-benzyl-4-(methoxymethyl)-4-piperidinyl]-N-phenylamine; 1-benzyl-4-(methoxymethyl)-N-phenyl-4-piperidinamine | C20H26N2O | 详情 | 详情 | |
| (V) | 33888 | N-[1-benzyl-4-(methoxymethyl)-4-piperidinyl]-N-phenylpropanamide | C23H30N2O2 | 详情 | 详情 | |
| (VI) | 32220 | N-[4-(methoxymethyl)-4-piperidinyl]-N-phenylpropanamide | C16H24N2O2 | 详情 | 详情 |