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Dobutamine hydrochloride, LY-46236, Posiject, Dobutrex

盐酸多巴酚丁胺 多巴酚丁胺 Chemical Name: (?-4-[2-[3-(4-Hydroxyphenyl)-1-methylpropylamino]ethyl]-1,2-benzenediol hydrochloride
CAS No. 49745-95-1, 34368-04-2 (free base)
项目整合开发状态: Launched-1977
项目研究机构: Lilly (Originator)
合成路线:The reduction of 4-(p-methoxyphenyl)-3-buten-2-one (II) with hydrogen over Raney-Ni in ethyl acetate gives the corresponding butanone (III),which is then condensed with homoveratrylamine (IV) in the same solvent to give the imine (V).This product,without isolation,is reduced again with hydrogen over Pd/C to yield 3,4-dimethoxy-N-[3-(4-hydroxyphenyl)-1-methylpropyl]-beta-phenylethylamine (I),which by demethylation with HBr in refluxing acetic acid.

合成路线:The Friedel-Crafts reaction of anisole (VI) with crotonyl chloride (VII) by means of AlCl3 in carbon disulfide gives p-methoxyphenyl propenyl ketone (VIII),which is then condensed with homoveratrylamine (IV) in toluene yielding 3-(3,4-dimethoxyphenylethylamino)-1-(4-methoxyphenyl)butan-1-one (IX).Finally,this ketone is reduced with hydrogen over Pd/C in ethanol to yield 3,4-dimethoxy-N-[3-(4-hydroxyphenyl)-1-methylpropyl]-beta-phenylethylamine (I),which by demethylation with HBr in refluxing acetic acid.

合成路线:The reaction of 4-(4-methoxyphenyl)-2-butylamine (X) with 3,4-dimethoxyphenylacetic acid (XI) at 200 C gives 2-(3,4-dimethoxyphenyl)-N-(4-methoxyphenyl-1-methyl-n-propyl)acetamide (XII),which is then reduced with borane in THF to yield 3,4-dimethoxy-N-[3-(4-hydroxyphenyl)-1-methylpropyl]-beta-phenylethylamine (I),which by demethylation with HBr in refluxing acetic acid.
📌 参考资料/链接:
参考文献标题:Dopamine derivatives
文献作者:Tuttle,R.R.; Mills,J.(Eli Lilly and Company)
参考来源:DE 2317710; ES 413639; FR 2182947; GB 1392674; JP 49007237

📄 详细内容


合成路线:The reduction of 4-(p-methoxyphenyl)-3-buten-2-one (II) with hydrogen over Raney-Ni in ethyl acetate gives the corresponding butanone (III),which is then condensed with homoveratrylamine (IV) in the same solvent to give the imine (V).This product,without isolation,is reduced again with hydrogen over Pd/C to yield 3,4-dimethoxy-N-[3-(4-hydroxyphenyl)-1-methylpropyl]-beta-phenylethylamine (I),which by demethylation with HBr in refluxing acetic acid.

合成路线:The Friedel-Crafts reaction of anisole (VI) with crotonyl chloride (VII) by means of AlCl3 in carbon disulfide gives p-methoxyphenyl propenyl ketone (VIII),which is then condensed with homoveratrylamine (IV) in toluene yielding 3-(3,4-dimethoxyphenylethylamino)-1-(4-methoxyphenyl)butan-1-one (IX).Finally,this ketone is reduced with hydrogen over Pd/C in ethanol to yield 3,4-dimethoxy-N-[3-(4-hydroxyphenyl)-1-methylpropyl]-beta-phenylethylamine (I),which by demethylation with HBr in refluxing acetic acid.

合成路线:The reaction of 4-(4-methoxyphenyl)-2-butylamine (X) with 3,4-dimethoxyphenylacetic acid (XI) at 200 C gives 2-(3,4-dimethoxyphenyl)-N-(4-methoxyphenyl-1-methyl-n-propyl)acetamide (XII),which is then reduced with borane in THF to yield 3,4-dimethoxy-N-[3-(4-hydroxyphenyl)-1-methylpropyl]-beta-phenylethylamine (I),which by demethylation with HBr in refluxing acetic acid.
参考文献标题:Dobutamine
文献作者:Castar,J.; Thorpe,P.
参考来源:Drugs Fut 1977,2(9),579


产品链接: CAS No. 49745-95-1››

产品链接: CAS No.34368-04-2››