methyl 1-benzyl-4-(propionylanilino)-4-piperidinecarboxylate -Drug Synthesis Database

【结构式】

【分子编号】49677

【品名】methyl 1-benzyl-4-(propionylanilino)-4-piperidinecarboxylate

【CA登记号】

【分子式】C₂₃H₂₈N₂O₃

【分子量】380.487

【元素组成】C 72.61% H 7.42% N 7.36% O 12.61%

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：(VIII)

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.

参考文献中间体

合成目标

【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