【药物名称】Vanoxerine hydrochloride, I-893, GBR-12909
化学结构式(Chemical Structure):
参考文献No.499
标题:Piperazine derivs., process for their preparation and their use
作者:Gootjes, J. (Gist-Brocades NV)
来源:DE 2755752; US 4202896
合成路线图解说明:

Condensation of bis(4-fluorophenyl)methyl 2-chloroethyl ether (I) with piperazine (II) in refluxing toluene afforded the monosubstituted piperazine (III). This was then alkylated with (3-bromopropyl)benzene (IV) in boiling EtOH to furnish the title compound.

参考文献No.65784
标题:Aryl 1,4-dialk(en)ylpiperazines as selective and very potent inhibitors of dopamine uptake
作者:Van der Zee, P.; et al.
来源:Eur J Med Chem 1980,15(4),363
合成路线图解说明:

Condensation of bis(4-fluorophenyl)methyl 2-chloroethyl ether (I) with piperazine (II) in refluxing toluene afforded the monosubstituted piperazine (III). This was then alkylated with (3-bromopropyl)benzene (IV) in boiling EtOH to furnish the title compound.

参考文献No.701678
标题:Scale-up synthesis of the dopamine uptake inhibitor GBR-12909
作者:Zhang, J.; Ironside, M.D.; Sugathapala, P.M.; Robertson, J.; Darey, M.C.P.
来源:Org Process Res Dev 2002,6(5),621
合成路线图解说明:

1-(3-Phenylpropyl)piperazine (III) has been obtained by condensation of 3-phenylpropyl bromide (I) with piperazine (II) in refluxing acetonitrile. The condensation of bis(4-fluorophenyl)methanol (IV) with 2-chloroethanol (V) by means of sulfuric acid gives the 2-chloroethyl bis(4-fluorophenyl)methyl ether (VI), which si treated with NaI to yield the corresponding iodo derivative (VII). Finally this compound is condensed with the intermediate piperazine (III) by means of aq. Na2CO3 to afford the target disubstituted piperazine.

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