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Timiperone, DD-3480, Tolopelon

替米哌隆Chemical Name: 1-(4-Fluorophenyl)-4-[4-(2-thioxo-2,3-dihydro-1H-benzimidazol-1-yl)piperidin-1-yl]butan-1-one
CAS No. 57648-21-2
项目整合开发状态: Launched
项目研究机构: Daiichi Pharmaceutical (Originator)
合成路线:By condesation of 4-chloro-1-(4-fluorophenyl)-1-butanone ethylene ketal (I) with 1-(4-piperidyl)-2-mercaptobenzimidazole (II) by means of KI in refluxing butanol

合成路线:The condensation of 4-chloro-1-(4-fluorophenyl)-1-butanone ethylene ketal (I) with 4-(2-nitroanilino)piperidine (III) by means of KI in refluxing butanol gives 1-[3-(4-fluorobenzoyl)propyl]-4-(2-nitroanilino)piperidine ethylene ketal (IV),which is reduced with H2 over Raney-Ni in methanol yielding the corresponding amino compound (V).Finally this compound is cyclized with CS2 by means of KOH in refluxing ethanol

合成路线: By reaction of 1-[1-[3-(4-fluorobenzoyl)propyl]-4-piperidyl]benzimidazol-2-one (VI) refluxing POCl3 to give 1-[1-[3-(4-fluorobenzoyl)propyl]-4-piperidyl]-2-chlorobenzimidazole (VII),which is refluxed with aqueous NaSH

合成路线:By heating a mixture of 1-[1-[3-(4-fluorobenzoyl)propyl]-4-piperidyl]benzimidazol-2-one (VI) and P2S5
📌 参考资料/链接:
参考文献标题:DD-3480
文献作者:Castar,J.; Blancafort,P.
参考来源:Drugs Fut 1978,3(6),451

📄 详细内容


合成路线:The reaction of adenosine-3',5'-cyclic phosphate (I) with butyric anhydride (II) in the presence of triethylamine gives N6,2'-O-dibutyryladenosine-3',5'-cyclic phosphate (III),which is then treated with Na-type Amberlite IR-120 B.

合成路线:The reaction of 2-(3-chloropropyl)-2-(4-fluorophenyl)-1,3-dioxolane (I) with 4-aminopyridine (II) gives the corresponding pyridinium salt (III),which is reduced with NaBH4 to 2-[3-(4-aminopiperidyl)propyl]-2-(4-fluorophenyl)-1,3-dioxolane (IV).The condensation of (IV) with 2-chloronitrobenzene (V) yields 2-[3-[4-(2-nitroanilino)piperidyl]propyl]-2-(4-fluorophenyl)-1,3-dioxolane (VI),which is hydrogenated with H2 over Raney-Ni affording the corresponding amino compound (VII).Finally this compound is cyclized with carbon disulfide and KOH

合成路线:The reaction of o-phenylenediamine (IX) with 4-chloropyridine (VIII) gives 2-(4-pyridylamino)aniline (X),which is condensed with 2-(3-chloropropyl)-2-(4-fluorophenyl)-1,3-dioxolane (I) to give the corresponding pyridinium salt (XI).The reduction of (XI) with NaBH4 yields amino compound (VII).Finally this compound is cyclized with carbon disulfide and KOH

参考文献标题:
文献作者:
参考来源:JP 76095096


合成路线:By condesation of 4-chloro-1-(4-fluorophenyl)-1-butanone ethylene ketal (I) with 1-(4-piperidyl)-2-mercaptobenzimidazole (II) by means of KI in refluxing butanol

合成路线:The condensation of 4-chloro-1-(4-fluorophenyl)-1-butanone ethylene ketal (I) with 4-(2-nitroanilino)piperidine (III) by means of KI in refluxing butanol gives 1-[3-(4-fluorobenzoyl)propyl]-4-(2-nitroanilino)piperidine ethylene ketal (IV),which is reduced with H2 over Raney-Ni in methanol yielding the corresponding amino compound (V).Finally this compound is cyclized with CS2 by means of KOH in refluxing ethanol

参考文献标题:
文献作者:Katsujiro,U.; et al.(Daiichi Seiyaku Co.,Ltd.)
参考来源:DE 2526393; GB 1467097; US 3963727


合成路线:The condensation of 4-chloro-1-(4-fluorophenyl)-1-butanone ethylene ketal (I) with 4-(2-nitroanilino)piperidine (III) by means of KI in refluxing butanol gives 1-[3-(4-fluorobenzoyl)propyl]-4-(2-nitroanilino)piperidine ethylene ketal (IV),which is reduced with H2 over Raney-Ni in methanol yielding the corresponding amino compound (V).Finally this compound is cyclized with CS2 by means of KOH in refluxing ethanol

参考文献标题:
文献作者:Katsujiro,U.; et al.(Daiichi Seiyaku Co.,Ltd.)
参考来源:BE 830171; ZA 7593577


合成路线:By condesation of 4-chloro-1-(4-fluorophenyl)-1-butanone ethylene ketal (I) with 1-(4-piperidyl)-2-mercaptobenzimidazole (II) by means of KI in refluxing butanol

参考文献标题:
文献作者:Sato,A.(Daiichi Seiyaku Co.,Ltd.)
参考来源:JP 7584578


合成路线:The condensation of 4-chloro-1-(4-fluorophenyl)-1-butanone ethylene ketal (I) with 4-(2-nitroanilino)piperidine (III) by means of KI in refluxing butanol gives 1-[3-(4-fluorobenzoyl)propyl]-4-(2-nitroanilino)piperidine ethylene ketal (IV),which is reduced with H2 over Raney-Ni in methanol yielding the corresponding amino compound (V).Finally this compound is cyclized with CS2 by means of KOH in refluxing ethanol

参考文献标题:
文献作者:Katsujiro,U.; et al.(Daiichi Seiyaku Co.,Ltd.)
参考来源:JP 7584579


合成路线:By heating a mixture of 1-[1-[3-(4-fluorobenzoyl)propyl]-4-piperidyl]benzimidazol-2-one (VI) and P2S5

参考文献标题:
文献作者:Sato,M.; et al.(Daiichi Seiyaku Co.,Ltd.)
参考来源:JP 76128974


产品链接: CAS No. 57648-21-2››