新产品编号:1144295
Chemical Name: 4-[1-(4-Phenylbutyl)piperidin-4-yl]phenol
项目整合开发状态: Preclinical
项目研究机构: Pfizer (Originator)
合成路线:The alkylation of 4-(4-methoxyphenyl)piperidine (I) with 4-phenylbutyl tosylate (II) provided the tertiary amine (III).The methyl ether group of (III) was then cleaved using BBr3 to furnish the title phenol.
📌 参考资料/链接：
参考文献标题:4-Substd.piperidine analogs and their use as subtype selective NMDA receptor antagonists
文献作者:Bigge,C.F.; Cai,S.X.; Weber,E.; Woodward,R.; Keana,J.F.W.; Lan,N.C.; Guzikowski,A.P.; Zhou,Z.-L.; Yeun,P.-W.(CoCensys,Inc.; Pfizer Inc.)
参考来源:EP 0869792; JP 2000500773; WO 9723216
📄 详细内容
合成路线:In an alternative procedure,lithiation of 4-(benzyloxy)-1-bromobenzene (IV),followed by addition of 1-benzyl-4-piperidone (V),gave piperidinol (VI).Subsequent treatment of (VI) with HCl produced dehydration of the tertiary alcohol and benzyl ether cleavage to give (VII).Double bond reduction and hydrogenolysis of the N-benzyl group of (VII) with H2 over Pd/C gave 4-(4-hydroxyphenyl)piperidine (VIII).This was finally alkylated with tosylate (II) to yield the title compound.
参考文献标题:Synthesis of N-substituted 4-(4-hydroxyphenyl)piperidines,4-(4-hydroxybenzyl)piperidines,and (?-3-(4-hydroxyphenyl)pyrrolidines: Selective antagonists at the 1A/2B NMDA receptor subtype
文献作者:Guzikowski,A.P.; Tamiz,A.P.; Acosta-Burruel,M.; Hong-Bae,S.; Cai,S.X.; Hawkinson,J.E.; Keana,J.F.; Kesten,S.R.; Shipp,C.T.; Tran,M.; Whittemore,E.R.; Woodward,R.M.; Wright,J.L.; Zhou,Z.L.
参考来源:J Med Chem 2000,43(5),984