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【结 构 式】

【分子编号】49674

【品名】4-Anilino-1-benzyl-4-cyanopiperidine

【CA登记号】

【 分 子 式 】C19H21N3

【 分 子 量 】291.39596

【元素组成】C 78.32% H 7.26% N 14.42%

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:(III)

The reaction of 1-benzyl-4-piperidone (I) with aniline (II) and KCN in acetic acid gives the aminonitrile (III), which is treated with H2SO4 at room temperature to yield the carboxamide (IV). The hydrolysis of (IV) with refluxing aqueous HCl affords the carboxylic acid (V), which is esterified with Ms-OH and methanol to provide the methyl ester (VI). Acylation of the NH group of (VI) with propionic anhydride (VII) gives the propionamide (VIII), which is debenzylated with H2 over Pd/C to yield the piperidine (IX). Finally, this compound is condensed with methyl acrylate (XI) in acetonitrile to afford the target compound.

1 Killgore, J.K.; Jacob, M. (Mallinckrodt Medical Inc.); New methods for the syntheses of alfentanil, sufentanil and remifentanil. WO 0140184 .
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) 12294 Aniline; Phenylamine 62-53-3 C6H7N 详情 详情
(III) 49674 4-Anilino-1-benzyl-4-cyanopiperidine C19H21N3 详情 详情
(IV) 49675 4-Anilino-1-benzylisonipecotamide C19H23N3O 详情 详情
(V) 33884 4-anilino-1-benzyl-4-piperidinecarboxylic acid C19H22N2O2 详情 详情
(VI) 49676 methyl 4-anilino-1-benzyl-4-piperidinecarboxylate C20H24N2O2 详情 详情
(VII) 20095 propionic anhydride 123-62-6 C6H10O3 详情 详情
(VIII) 49677 methyl 1-benzyl-4-(propionylanilino)-4-piperidinecarboxylate C23H28N2O3 详情 详情
(IX) 15668 methyl 4-(propionylanilino)-4-piperidinecarboxylate C16H22N2O3 详情 详情
(X) 14156 methyl acrylate 96-33-3 C4H6O2 详情 详情
Extended Information