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Ambroxol hydrochloride, NA-872, Mucosolvan, Mucosolvan-L, Mucosal-L, Ponophen

盐酸氨溴索 氨溴索 Chemical Name: trans-4-(2-Amino-3,5-dibromobenzylamino)cyclohexanol hydrochloride
CAS No. 23828-92-4, 18683-91-5 (free base)
项目整合开发状态: Launched
项目研究机构: NicOx (Originator), Boehringer Ingelheim (Not Determined), Teijin (Not Determined)
合成路线:By condensation of trans-4-aminocyclohexanol (I) with isatoic anhydride (II) in hot (100 C) xylene to give 2-amino-N-(trans-4-hydroxycyclohexyl)benzamide (III) ,m.p.219.5-220 C,which is reduced with LiAlH4 in THF to (trans-4-hydroxycyclohexyl)(2-aminobenzyl)amine (IV) (oxalate,m.p.185-6 C); this product is finally brominated with Br2 in acetic acid.
📌 参考资料/链接:
参考文献标题:Pharmaceutical compositions for use in the treatment of certain respiratory diseases or conditions in prematurely born children
文献作者:Keck,J.; et al.(Dr.Karl Thomae GmbH)
参考来源:BE 0795585; DE 2207460; FR 2181742; GB 1420976

📄 详细内容


合成路线:By condensation of trans-4-aminocyclohexanol (I) with isatoic anhydride (II) in hot (100 C) xylene to give 2-amino-N-(trans-4-hydroxycyclohexyl)benzamide (III) ,m.p.219.5-220 C,which is reduced with LiAlH4 in THF to (trans-4-hydroxycyclohexyl)(2-aminobenzyl)amine (IV) (oxalate,m.p.185-6 C); this product is finally brominated with Br2 in acetic acid.

参考文献标题:N-(Hydroxycyclohexyl)aminobenzylamines and the salts thereof
文献作者:Keck,J.; et al.(Boehringer Ingelheim GmbH)
参考来源:ES 340219; FR 1522709; GB 1178034; US 3536713


合成路线:By condensation of trans-4-aminocyclohexanol (I) with isatoic anhydride (II) in hot (100 C) xylene to give 2-amino-N-(trans-4-hydroxycyclohexyl)benzamide (III) ,m.p.219.5-220 C,which is reduced with LiAlH4 in THF to (trans-4-hydroxycyclohexyl)(2-aminobenzyl)amine (IV) (oxalate,m.p.185-6 C); this product is finally brominated with Br2 in acetic acid.

参考文献标题:
文献作者:Kech,J.
参考来源:Liebigs Ann Chem 1967,707(19,Suppl.2),107


合成路线:By condensation of trans-4-aminocyclohexanol (I) with isatoic anhydride (II) in hot (100 C) xylene to give 2-amino-N-(trans-4-hydroxycyclohexyl)benzamide (III) ,m.p.219.5-220 C,which is reduced with LiAlH4 in THF to (trans-4-hydroxycyclohexyl)(2-aminobenzyl)amine (IV) (oxalate,m.p.185-6 C); this product is finally brominated with Br2 in acetic acid.

合成路线:By condensation of trans-4-aminocyclohexanol (I) with 2-amino-3,5-dibromo-benzaldehyde (V) by means of formic acid at 200 C.When the condensation of the aminoalcohol (I) and the aldehyde (V) is performed with KOH in ethanol,the intermediate N-(2-amino-3,5-dibromobenzylidene)-trans-4-aminocyclohexanol (VI),m.p.124.0-5.5 C is obtained,which is then reduced with NaBH4 in ethanol.

参考文献标题:Ambroxol
文献作者:Castar,J.; Armstrong,B.
参考来源:Drugs Fut 1976,1(3),959


合成路线:By condensation of trans-4-aminocyclohexanol (I) with 2-amino-3,5-dibromo-benzaldehyde (V) by means of formic acid at 200 C.When the condensation of the aminoalcohol (I) and the aldehyde (V) is performed with KOH in ethanol,the intermediate N-(2-amino-3,5-dibromobenzylidene)-trans-4-aminocyclohexanol (VI),m.p.124.0-5.5 C is obtained,which is then reduced with NaBH4 in ethanol.

参考文献标题:Neues Verfahren zur Herstellung von N-(trans-4-Hydroxycyclohexyl)-(2-amino-3,5-dibromobenzyl)amin
文献作者:Keck,J.; et al.
参考来源:DE 2218647; ES 413827; ES 421120; JP 49014443


合成路线:By condensation of trans-4-aminocyclohexanol (I) with 2-amino-3,5-dibromo-benzaldehyde (V) by means of formic acid at 200 C.When the condensation of the aminoalcohol (I) and the aldehyde (V) is performed with KOH in ethanol,the intermediate N-(2-amino-3,5-dibromobenzylidene)-trans-4-aminocyclohexanol (VI),m.p.124.0-5.5 C is obtained,which is then reduced with NaBH4 in ethanol.
参考文献标题:Neues Verfahren zur Herstellung von 2-Aminobenzylaminen
文献作者:Keck,J.; et al.
参考来源:DE 2223193; ES 414671; JP 49048624; JP 53116339; JP 53149944


产品链接: CAS No. 23828-92-4››

产品链接: CAS No.18683-91-5››