1-benzyl-4-phenyl-4-piperidinylformamide -Drug Synthesis Database

【结构式】

【分子编号】59286

【品名】1-benzyl-4-phenyl-4-piperidinylformamide

【CA登记号】

【分子式】C₁₉H₂₂N₂O

【分子量】294.39656

【元素组成】C 77.52% H 7.53% N 9.52% O 5.43%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(XL)

In a further method, aminopiperidine (IV) was converted to the formamide (XL) by heating in ethyl formate. Formyl group reduction in (XL) with LiAlH4 provided the N-metyl amine (XLI). The N-benzyl group of (XLI) was then removed by catalytic hydrogenation over Pd/C. Alkylation of the resultant piperidine (XLII) with mesylate (XXVII) gave adduct (XLIII). After acetylation of (XLIII) in neat Ac2O, the racemic mixture was separated by chiral HPLC.

参考文献中间体

合成目标

【1】 Giardina, G.A.M.; et al.; A reliable and efficient synthesis of SR 142801. Bioorg Med Chem Lett 1996, 6, 19, 2307.
【2】 Grugni, M.; Rigolio, R.; Erhard, K.F. (GlaxoSmithKline Inc.; GlaxoSmithKline SpA); Process for the preparation of 3,3-disubstd. piperidines. WO 9805640 .

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(IV)	54994	1-benzyl-4-phenyl-4-piperidinylamine; 1-benzyl-4-phenyl-4-piperidinamine	C₁₈H₂₂N₂	详情	详情
(XXVII)	59278	3-[1-benzoyl-3-(3,4-dichlorophenyl)-3-piperidinyl]propyl methanesulfonate	C₂₂H₂₅Cl₂NO₄S	详情	详情
(XL)	59286	1-benzyl-4-phenyl-4-piperidinylformamide	C₁₉H₂₂N₂O	详情	详情
(XLI)	59287	1-benzyl-N-methyl-4-phenyl-4-piperidinamine; N-(1-benzyl-4-phenyl-4-piperidinyl)-N-methylamine	C₁₉H₂₄N₂	详情	详情
(XLII)	59288	N-methyl-4-phenyl-4-piperidinamine; N-methyl-N-(4-phenyl-4-piperidinyl)amine	C₁₂H₁₈N₂	详情	详情
(XLIII)	59289	(3-(3,4-dichlorophenyl)-3-{3-[4-(methylamino)-4-phenyl-1-piperidinyl]propyl}-1-piperidinyl)(phenyl)methanone	C₃₃H₃₉Cl₂N₃O	详情	详情

合成路线2

该中间体在本合成路线中的序号：(XL)

A new method has been reported. Formamide (XL) was prepared form carbinol (II) by a modified Ritter reaction with cyanotrimethylsilane. Subsequent reduction of (XL) with LiAlH4 gave the N-methyl amine (XLI), which was converted to acetamide (XLIV) by treatment with acetyl chloride. Benzyl group hydrogenolysis in (XLIV) afforded the piperidine (X). Finally, alkylation of piperidine (X) with the chiral alkyl iodide (XXXV) provided the title compound.

参考文献中间体

合成目标

【1】 Chen, H.G.; et al.; A practical and scalable synthesis of SR 142801, a tachykinin NK3 antagonist. Bioorg Med Chem Lett 1997, 7, 5, 555.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(II)	29470	1-benzyl-4-phenyl-4-piperidinol	C₁₈H₂₁NO	详情	详情
(X)	59267	N-methyl-N-(4-phenyl-4-piperidinyl)acetamide	C₁₄H₂₀N₂O	详情	详情
(XXXV)	29469	[(3S)-3-(3,4-dichlorophenyl)-3-(3-iodopropyl)piperidinyl](phenyl)methanone	C₂₁H₂₂Cl₂INO	详情	详情
(XL)	59286	1-benzyl-4-phenyl-4-piperidinylformamide	C₁₉H₂₂N₂O	详情	详情
(XLI)	59287	1-benzyl-N-methyl-4-phenyl-4-piperidinamine; N-(1-benzyl-4-phenyl-4-piperidinyl)-N-methylamine	C₁₉H₂₄N₂	详情	详情
(XLIV)	59290	N-(1-benzyl-4-phenyl-4-piperidinyl)-N-methylacetamide	C₂₁H₂₆N₂O	详情	详情

Extended Information