【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% |
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 |