Picumast dihydrochloride, BM-15100, Auteral
2H-1-苯并吡喃-2-1,7-[3-[4-[(4-氯苯基)甲基]-1-吡嗪基丙氧盐]-3,4-二甲基-盐酸盐(1:2)Chemical Name: 1-(4-Chlorobenzyl)-4-[3-(3,4-dimethylcoumarin-7-yloxy)propyl]piperazine dihydrochloride; 7-[3-[4-[(4-Chlorophenyl)methyl]-1-piperazinyl]propoxy]-3,4-dimethyl-2H-1-benzopyran-2-one dihydrochloride; 3,4-Dimethyl-7-[4-(4-chlorophenyl)methyl-1-piperazinyl]propoxycoumarin dihydrochloride
CAS No. 39577-20-3, 39557-19-2 (free base)
项目整合开发状态: Phase III
项目研究机构: Roche (Originator)
合成路线:By condensation of 7-hydroxy-3,4-dimethylcoumarin (I) with 1-(3-chloropropyl)-4-(4-chlorobenzyl)piperazine (II) by means of K2CO3 and KI in refluxing butanone.
📌 参考资料/链接：
参考文献标题:Coumarin-7-yloxyalkyl piperazine compounds
文献作者:Witte,E.C.; et al.(Boehringer Ingelheim GmbH)
参考来源:DE 2123924; FR 2137731; GB 1335946; JP 58219176; US 3810898
📄 详细内容
合成路线:The total synthesis of picumast dihydrochloride has been described:The alkylation of piperazine (I) with 4-chlorobenzyl chloride (II) in ethanol gives 1-(4-chlorobenzyl)piperazine (III),which is alkylated again with 1-bromo-3-chloropropane (IV) by means of triethylamine in a suitable solvent to yield 1-(4-chlorobenzyl)-4-(3-chloropropyl)piperazine (V).Finally,this compound is condensed with 7-hydroxy-3,4-dimethylcoumarin (VI) by means of K2CO3 in refluxing butanone.Compound (VI) is obtained by cyclization of resorcinol (VII) with ethyl 2-methylacetoacetate (VIII) by means of refluxing acetic acid containing HCl.
参考文献标题:Chemical synthesis of picumast dihydrochloride
文献作者:Witte,E.-C.
参考来源:Arzneim-Forsch Drug Res 1989,39(10a),1309
合成路线:By condensation of 7-hydroxy-3,4-dimethylcoumarin (I) with 1-(3-chloropropyl)-4-(4-chlorobenzyl)piperazine (II) by means of K2CO3 and KI in refluxing butanone.
参考文献标题:BM-15100
文献作者:Hillier,K.; Castar,J.
参考来源:Drugs Fut 1977,2(7),438
产品链接: CAS No. 39577-20-3››