4-(3,4-dichlorophenyl)-1-methyl-4-piperidinecarbonitrile -Drug Synthesis Database

【结构式】

【分子编号】47010

【品名】4-(3,4-dichlorophenyl)-1-methyl-4-piperidinecarbonitrile

【CA登记号】

【分子式】C₁₃H₁₄Cl₂N₂

【分子量】269.17304

【元素组成】C 58.01% H 5.24% Cl 26.34% N 10.41%

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：(IV)

Dialkylation of 2-aryl acetonitrile (I) with bromoacetaldehyde dimethyl acetal (II) by means of NaNH2 in toluene provides diacetal (III), which is cyclized to cyanopiperidine derivative (IV) by first hydrolysis of the acetal groups with HCl, followed by reductive amination with methylamine in the presence of NaBH3CN in MeOH. Finally, the target product is obtained by hydrolysis of the nitrile group of (IV) with aqueous H2SO4, followed by esterification performed by heating with EtOH.

参考文献中间体

合成目标

【1】 katz, J.L.; Trudell, M.L.; Lomenzo, S.A.; Kopajtic, T.; Gerdes, R.M.; Izenwasser, S.; Synthesis, dopamine and serotonin transporter binding affinities of novel analogues of meperidine. Bioorg Med Chem Lett 1999, 9, 23, 3273.

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)	26935	2-(3,4-dichlorophenyl)acetonitrile	3218-49-3	C₈H₅Cl₂N	详情	详情
(II)	13183	2-Bromo-1,1-dimethoxyethane; 2-Bromo-1-methoxyethyl methyl ether; Bromoacetaldehyde dimethyl acetal	7252-83-7	C₄H₉BrO₂	详情	详情
(III)	47009	2-(3,4-dichlorophenyl)-2-(2,2-dimethoxyethyl)-4,4-dimethoxybutanenitrile		C₁₆H₂₁Cl₂NO₄	详情	详情
(IV)	47010	4-(3,4-dichlorophenyl)-1-methyl-4-piperidinecarbonitrile		C₁₃H₁₄Cl₂N₂	详情	详情

Extended Information