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【结 构 式】

【分子编号】33888

【品名】N-[1-benzyl-4-(methoxymethyl)-4-piperidinyl]-N-phenylpropanamide

【CA登记号】

【 分 子 式 】C23H30N2O2

【 分 子 量 】366.50348

【元素组成】C 75.38% H 8.25% N 7.64% O 8.73%

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:(V)

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
Extended Information