【药物名称】Dobutamine hydrochloride, LY-46236, Posiject, Dobutrex
化学结构式(Chemical Structure):
参考文献No.47815
标题:Dopamine derivatives
作者:Tuttle, R.R.; Mills, J. (Eli Lilly and Company)
来源:DE 2317710; ES 413639; FR 2182947; GB 1392674; JP 49007237
合成路线图解说明:

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.

合成路线图解说明:

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.

合成路线图解说明:

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No.800684
标题:Dobutamine
作者:Casta馿r, J.; Thorpe, P.
来源:Drugs Fut 1977,2(9),579
合成路线图解说明:

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.

合成路线图解说明:

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.

合成路线图解说明:

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.

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