2-[4-methoxy-3-(phenethyloxy)phenyl]-N,N-dipropylacetamide -Drug Synthesis Database

【结构式】

【分子编号】23686

【品名】2-[4-methoxy-3-(phenethyloxy)phenyl]-N,N-dipropylacetamide

【CA登记号】

【分子式】C₂₃H₃₁NO₃

【分子量】369.50408

【元素组成】C 74.76% H 8.46% N 3.79% O 12.99%

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：(X)

Isovanillin (I) was alkylated with phenethyl bromide (II) in the presence of K2CO3 to afford phenethyl ether (III). The aldehyde function of (III) was then reduced with NaBH4, and the resulting alcohol (IV) was converted to chloride (V) by means of SOCl2 in THF-DMF. Subsequent displacement of the chlorine atom of (V) by KCN afforded nitrile (VI), which was hydrolyzed to acid (VII) with KOH in aqueous EtOH. Further conversion of (VII) to acid chloride (VIII), followed by condensation with dipropyl amine (IX) in toluene provided amide (X). Finally, reduction with LiAlH4 gave the corresponding amine, that was isolated as the hydrochloride salt.

参考文献中间体

合成目标

【1】 Nakazato, A.; et al.; Design, synthesis, structure-activity relationship. J Med Chem 1999, 42, 6, 1076.

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)	18455	3-hydroxy-4-methoxybenzaldehyde; Isovanillin	621-59-0	C₈H₈O₃	详情	详情
(II)	20730	1-(2-bromoethyl)benzene；1-Bromo-2-phenylethane;(2-Bromoethyl)benzene;Phenethyl bromide	103-63-9	C₈H₉Br	详情	详情
(III)	23679	4-methoxy-3-(phenethyloxy)benzaldehyde		C₁₆H₁₆O₃	详情	详情
(IV)	23680	[4-methoxy-3-(phenethyloxy)phenyl]methanol		C₁₆H₁₈O₃	详情	详情
(V)	23681	4-(chloromethyl)-1-methoxy-2-(phenethyloxy)benzene; 5-(chloromethyl)-2-methoxyphenyl phenethyl ether		C₁₆H₁₇ClO₂	详情	详情
(VI)	23682	2-[4-methoxy-3-(phenethyloxy)phenyl]acetonitrile		C₁₇H₁₇NO₂	详情	详情
(VII)	23683	2-[4-methoxy-3-(phenethyloxy)phenyl]acetic acid		C₁₇H₁₈O₄	详情	详情
(VIII)	23685	2-[4-methoxy-3-(phenethyloxy)phenyl]acetyl chloride		C₁₇H₁₇ClO₃	详情	详情
(IX)	21856	N,N-dipropylamine; N-propyl-1-propanamine	142-84-7	C₆H₁₅N	详情	详情
(X)	23686	2-[4-methoxy-3-(phenethyloxy)phenyl]-N,N-dipropylacetamide		C₂₃H₃₁NO₃	详情	详情

Extended Information