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【结 构 式】

【分子编号】41699

【品名】(E)-3-(3,4-dimethylphenyl)-2-propenenitrile

【CA登记号】

【 分 子 式 】C11H11N

【 分 子 量 】157.21508

【元素组成】C 84.04% H 7.05% N 8.91%

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:(VII)

The 2-chloroethylation of ethyl homovanillate (I) with 1-bromo-2-chloroethane and K2CO3 in acetone gives ethyl 2-[4-(2-chloroethoxy)-3-methoxyphenyl]acetate (II), which is treated with sodium azide in toluene followed by hydrolysis with aqueous NaOH in MeOH, yielding 2-[4-(2-azidoethoxy)-3-methoxyphenyl]acetic acid (IV). The reaction of (IV) with SOCl2 and Et3N affords the acyl chloride (V). The reaction of 3-iodo-o-xylene (VI) and acrylonitrile under the Heck reaction conditions [Pd(OAc)2, tri-o-tolylphosphine and Et3N in MeCN] gives an isomeric mixture of 3-(3,4-dimethyl-phenyl)-2-propenenitrile (VII), which is hydrogenated with Pd/C followed by Raney-Ni to provide 3-(3,4-dimethylphenyl)propylamine (IX). The coupling reaction between the acyl chloride (V) and amine (IX) with Et3N in CH2Cl2 gives the amide (X). Finally, Pd/C catalyzed hydrogenation of this compound affords 2-[4-(2-aminoethoxy)-3-methoxyphenyl]-N-[3-(3,4-dimethylphenyl)propyl]acetamide.

1 Lee, C.W.; Park, N.S.; Seong, C.M.; Jung, Y.S.; Baek, G.H.; Cho, S.J.; Synthesis of 3-arylpropylamine derivatives from aryl halides using Heck reaction. Bull Korean Chem Soc 1999, 20, 232-236.
2 Park, N.S.; Kim, W.B.; Kim, S.H.; Seong, C.M.; Jung, Y.S.; DA-5018. Drugs Fut 2000, 25, 11, 1131.
3 Lee, K.S.; Choi, J.K.; Hong, M.S.; Kim, H.S.; Lim, H.J.; Ha, D.C.; Park, N.S. (Korea Research Institute of Chemical Technology); Novel phenylacetamide derivs. and processes for the preparation thereof. EP 0525360; US 5242944 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
10847 Acrylonitrile 107-13-1 C3H3N 详情 详情
(I) 41693 ethyl 2-(4-hydroxy-3-methoxyphenyl)acetate C11H14O4 详情 详情
(II) 41694 ethyl 2-[4-(2-chloroethoxy)-3-methoxyphenyl]acetate C13H17ClO4 详情 详情
(III) 41695 ethyl 2-[4-(2-azidoethoxy)-3-methoxyphenyl]acetate C13H17N3O4 详情 详情
(IV) 41696 2-[4-(2-azidoethoxy)-3-methoxyphenyl]acetic acid C11H13N3O4 详情 详情
(V) 41697 2-[4-(2-azidoethoxy)-3-methoxyphenyl]acetyl chloride C11H12ClN3O3 详情 详情
(VI) 41698 4-iodo-1,2-dimethylbenzene 31599-61-8 C8H9I 详情 详情
(VII) 41699 (E)-3-(3,4-dimethylphenyl)-2-propenenitrile C11H11N 详情 详情
(VIII) 41700 3-(3,4-dimethylphenyl)propanenitrile C11H13N 详情 详情
(IX) 40288 3-(3,4-dimethylphenyl)-1-propanamine; 3-(3,4-dimethylphenyl)propylamine C11H17N 详情 详情
(X) 40292 2-[4-(2-azidoethoxy)-3-methoxyphenyl]-N-[3-(3,4-dimethylphenyl)propyl]acetamide C22H28N4O3 详情 详情
Extended Information