Gastrophenzine, DZO-200, AN5
氨基甲酸,[4-(4-氯苯基)-1,2,3,4-四氢-2-甲基-8-异喹啉基]-,乙酯,一盐酸盐(9CI)Chemical Name: 4-(4-Chlorophenyl)-8-(ethoxycarbonylamino)-2-methyl-1,2,3,4-tetrahydroisoquinoline monohydrochloride; [4-(4-Chlorophenyl)-2-methyl-1,2,3,4-tetrahydro-8-isoquinolinyl]carbamic acid ethyl ester monohydrochloride
CAS No. 89845-17-0
项目整合开发状态: Preclinical
项目研究机构: Egis (Originator), Pharmachim (Originator)
合成路线:Two related methods have been described:The alkylation of 2-nitrobenzylmethylamine (I) with p-chlorphenyloxyran (II) in boiling ethanol affords N-(2-nitrobenzyl)-2-(methylamino)-1-(4-chlorphenyl)-1-ethanol (III),which is further reduced via NaBH4/NiCl2 in boiling methanol to N-(2-aminobenzyl)-2-(methylamino)-1-(4-chlorphenyl)-1-ethanol (IV).The acylation of (IV) with ethyl chloroformate in the presence of pyridine and in a medium of benzene - DMFA (Method A) results in N-[2-(ethoxycarbonyl)amino]-2-(methylamino)-1-(4-chlorophenyl)-1-ethanol (V).The latter is cyclodehydrated by means of conc.H2SO4 in dichloroethane.According to method B,the amino alcohol (IV) is cyclodehydrated by conc.H2SO4 to 8-amino-4-(4-chlorophenyl)-2-methyl-1,2,3-4-tetrahydroisoquinoline (VI),which is acylated with ethyl chloroformate in boiling benzene.
📌 参考资料/链接：
参考文献标题:Gastrophenzine
文献作者:Ivanova,N.; Angelova,J.; Mondeshka,D.; Ivanov,C.
参考来源:Drugs Fut 1992,17(2),104
📄 详细内容
合成路线:Two related methods have been described:The alkylation of 2-nitrobenzylmethylamine (I) with p-chlorphenyloxyran (II) in boiling ethanol affords N-(2-nitrobenzyl)-2-(methylamino)-1-(4-chlorphenyl)-1-ethanol (III),which is further reduced via NaBH4/NiCl2 in boiling methanol to N-(2-aminobenzyl)-2-(methylamino)-1-(4-chlorphenyl)-1-ethanol (IV).The acylation of (IV) with ethyl chloroformate in the presence of pyridine and in a medium of benzene - DMFA (Method A) results in N-[2-(ethoxycarbonyl)amino]-2-(methylamino)-1-(4-chlorophenyl)-1-ethanol (V).The latter is cyclodehydrated by means of conc.H2SO4 in dichloroethane.According to method B,the amino alcohol (IV) is cyclodehydrated by conc.H2SO4 to 8-amino-4-(4-chlorophenyl)-2-methyl-1,2,3-4-tetrahydroisoquinoline (VI),which is acylated with ethyl chloroformate in boiling benzene.
参考文献标题:Synthesis,stereochemistry,and antiulcer activity of 4-phenyltetrahydroisoquinolines
文献作者:Ivanova,N.; Ivanov,T.; Mondeshka,D.; Berova,N.; Angelova,I.; Rakovska,R.; Bojadjiev,S.; Tancheva,C.; Tascheva,D.
参考来源:Arch Pharm 1990,323(1),3
产品链接: CAS No. 89845-17-0››