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【结 构 式】

【药物名称】

【化学名称】4-(3-Chlorophenylsulfanyl)piperidine hydrochloride

【CA登记号】

【 分 子 式 】C11H15Cl2NS

【 分 子 量 】264.2189

【开发单位】

【药理作用】 

合成路线1

Nucleophilic substitution of 2,4-dichloronitrobenzene (I) with 1-methylpiperidin-4-thiol (II) in the presence of K2CO3 provided a mixture of sulfides (III) and (IV), from which the major isomer (IV) was isolated by crystallization from EtOH. The nitro group of (IV) was then reduced with iron under acidic conditions to the corresponding amine (V). Subsequent diazotization of (V) and reduction of the diazonium salt (VI) with EtOH led to the deaminated compound (VII). N-Demethylation of (VII) was achieved by treatment with ethyl chloroformate, yielding the N-ethoxycarbonyl derivative (VIII). Finally, acid hydrolysis of carbamate (VIII) provided the target amine, which was isolated as the hydrochloride salt.

1 Proska, J.; Radl, S.; Krejci, I.; Hezky, P.; Synthesis and analgesic activity of some deaza derivatives of anpirtoline. Arch Pharm 1999, 332, 1, 13.
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) 21787 2,4-dichloro-1-nitrobenzene 611-06-3 C6H3Cl2NO2 详情 详情
(II) 21788 1-methyl-4-piperidinethiol; 1-methyl-4-piperidinylhydrosulfide C6H13NS 详情 详情
(III) 21789 4-[(3-chloro-4-nitrophenyl)sulfanyl]-1-methylpiperidine; 3-chloro-4-nitrophenyl 1-methyl-4-piperidinyl sulfide C12H15ClN2O2S 详情 详情
(IV) 21790 4-[(5-chloro-2-nitrophenyl)sulfanyl]-1-methylpiperidine; 5-chloro-2-nitrophenyl 1-methyl-4-piperidinyl sulfide C12H15ClN2O2S 详情 详情
(V) 21791 4-chloro-2-[(1-methyl-4-piperidinyl)sulfanyl]phenylamine; 4-chloro-2-[(1-methyl-4-piperidinyl)sulfanyl]aniline C12H17ClN2S 详情 详情
(VI) 21792 4-[[5-chloro-2-(1lambda(5)-diazynyl)phenyl]sulfanyl]-1-methylpiperidine; 5-chloro-2-(1lambda(5)-diazynyl)phenyl 1-methyl-4-piperidinyl sulfide C12H16ClN3S 详情 详情
(VII) 21793 4-[(3-chlorophenyl)sulfanyl]-1-methylpiperidine; 3-chlorophenyl 1-methyl-4-piperidinyl sulfide C12H16ClNS 详情 详情
(VIII) 21794 ethyl 4-[(3-chlorophenyl)sulfanyl]-1-piperidinecarboxylate C14H18ClNO2S 详情 详情
Extended Information