(4-anilino-1-benzyl-4-piperidinyl)methanol -Drug Synthesis Database

【结构式】

【分子编号】33886

【品名】(4-anilino-1-benzyl-4-piperidinyl)methanol

【CA登记号】

【分子式】C₁₉H₂₄N₂O

【分子量】296.41244

【元素组成】C 76.99% H 8.16% N 9.45% O 5.4%

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 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.

参考文献中间体

合成目标

【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