3-[(3,4-dimethoxyphenethyl)amino]-1-(4-methoxyphenyl)-1-butanone -Drug Synthesis Database

【结构式】

【分子编号】40180

【品名】3-[(3,4-dimethoxyphenethyl)amino]-1-(4-methoxyphenyl)-1-butanone

【CA登记号】

【分子式】C₂₁H₂₇NO₄

【分子量】357.44972

【元素组成】C 70.56% H 7.61% N 3.92% O 17.9%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号：(IX)

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.

参考文献中间体

合成目标

【1】 Castaner, J.; Thorpe, P.; Dobutamine. Drugs Fut 1977, 2, 9, 579.
【2】 Tuttle, R.R.; Mills, J. (Eli Lilly and Company); Dopamine derivatives. DE 2317710; ES 413639; FR 2182947; GB 1392674; JP 49007237 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	40177	N-(3,4-dimethoxyphenethyl)-4-(4-methoxyphenyl)-2-butanamine; N-(3,4-dimethoxyphenethyl)-N-[3-(4-methoxyphenyl)-1-methylpropyl]amine		C₂₁H₂₉NO₃	详情	详情
(IV)	10098	2-(3,4-Dimethoxyphenyl)-1-ethanamine; 3,4-Dimethoxyphenethylamine; 2-(3,4-Dimethoxyphenyl)ethylamine	120-20-7	C₁₀H₁₅NO₂	详情	详情
(VI)	23767	Methoxybenzene; Methyl phenyl ether; Anisole	100-66-3	C₇H₈O	详情	详情
(VII)	40178	(E)-2-Butenoyl chloride; (E)-Crotonyl chloride	625-35-4	C₄H₅ClO	详情	详情
(VIII)	40179	(E)-1-(4-methoxyphenyl)-2-buten-1-one		C₁₁H₁₂O₂	详情	详情
(IX)	40180	3-[(3,4-dimethoxyphenethyl)amino]-1-(4-methoxyphenyl)-1-butanone		C₂₁H₂₇NO₄	详情	详情

Extended Information