JJC-1-059
Chemical Name: cis-N-[3-[3,5-Dimethyl-4-(3-phenylpropyl)-1-piperazinyl]propyl]-N,N-Bis(4-fluorophenyl)amine
项目整合开发状态: Preclinical
项目研究机构: National Institute on Drug Abuse (Originator)
合成路线:The CuI-assisted coupling between methyl N-(4-fluorophenyl)carbamate (I) and 1-bromo-4-fluorobenzene (II) produced the N,N-bis(4-fluorophenyl)carbamate (III),which was subsequently hydrolyzed to bis(4-fluorophenyl)amine (IV) using ethanolic KOH.Acylation of diarylamine (IV) with 3-bromopropionyl chloride (V) gave bromopropionamide (VI).This was then condensed with cis-2,6-dimethylpiperazine (VII) to yield the 3-piperazinylpropionamide (VIII).Amide reduction with LiAlH4 provided the triamino compound (IX).Acid chloride (XI),prepared from hydrocinnamic acid (X),was then coupled with piperazine (IX) to furnish amide (XII).The amide function was finally reduced to the corresponding amine by using LiAlH4.
📌 参考资料/链接：
参考文献标题:[3-cis-3,5-Dimethyl-1-piperazinyl)alkyl]-bis-(4'-fluorophenyl)amines analogs as novel probes for the dopamine transporter
文献作者:Ca,J.; Newman,A.H.; Kopajtic,T.; Katz,J.L.; Husbands,S.M.
参考来源:221st ACS Natl Meet (April 1 2001,San Diego) 2001,Abst MEDI 96
📄 详细内容
合成路线:The CuI-assisted coupling between methyl N-(4-fluorophenyl)carbamate (I) and 1-bromo-4-fluorobenzene (II) produced the N,N-bis(4-fluorophenyl)carbamate (III),which was subsequently hydrolyzed to bis(4-fluorophenyl)amine (IV) using ethanolic KOH.Acylation of diarylamine (IV) with 3-bromopropionyl chloride (V) gave bromopropionamide (VI).This was then condensed with cis-2,6-dimethylpiperazine (VII) to yield the 3-piperazinylpropionamide (VIII).Amide reduction with LiAlH4 provided the triamino compound (IX).Acid chloride (XI),prepared from hydrocinnamic acid (X),was then coupled with piperazine (IX) to furnish amide (XII).The amide function was finally reduced to the corresponding amine by using LiAlH4.
参考文献标题:[3-cis-3,5-Dimethyl-(1-piperazinyl)alkyl]-bis-(4'-fluorophenyl)amine analogues as novel for the dopamine transporter
文献作者:Cao,J.; Husbands,S.M.; Kopajtic,T.; Katz,J.L.; Newman,A.H.
参考来源:Bioorg Med Chem Lett 2001,11(24),3169