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【结 构 式】 
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【药物名称】SAL-V-11 【化学名称】4-(3,4-Dichlorophenyl)-1-methylpiperidine-4-carboxylic acid ethyl ester hydrochloride 【CA登记号】258500-91-3 (free base) 【 分 子 式 】C15H20Cl3NO2 【 分 子 量 】352.69115 |
【开发单位】National Institute on Drug Abuse (Originator) 【药理作用】Pharmacological Tools, 5-HT Reuptake Inhibitors, Dopamine Reuptake Inhibitors |
合成路线1
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.
| 【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 |