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【结 构 式】

【分子编号】10364

【品名】3,4-dibromobutanenitrile

【CA登记号】

【 分 子 式 】C4H5Br2N

【 分 子 量 】226.89844

【元素组成】C 21.17% H 2.22% Br 70.43% N 6.17%

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:(II)

A new synthesis of centperazine has been reported: The cyclization of N,N'-dibenzylethylenediamine (I) with 2,3-dibromopropionitrile (II) by means of triethylamine in refluxing toluene gives 2-(1,4-dibenzylpiperazin-2-yl)acetonitrile (III), which is reduced with H2 over RaNi in methanol to yield the corresponding ethylamine (IV). Acylation of (IV) with ethyl chloroformate (V) and triethylamine in dichloromethane affords the corresponding carbamate (VI), which is debenzylated by hydrogenation with H2 over Pd/C in acetic acid, giving N-[2-(2-piperazinyl)ethyl]carbamic acid ethyl ester (VII). The cyclization of (VII) by means of sodium ethoxide in hot ethanol yields perhydropyrazino[1,2-c]pyrimidin-6-one (VIII), which is methylated with formaldehyde-formic acid to the 2-methyl derivative (IX). Finally, this compound is ethylated with ethyl iodide, tetrabutylammonium bromide and KOH in THF.

1 Chatterjee, S.K.; Sahu, D.P.; Sengupta, S.; A convenient synthesis of centperazine, an antifilarial candidate drug. Liebigs Ann Chem 1993, 4, 4, 437.
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) 18340 N(1),N(2)-dibenzyl-1,2-ethanediamine; N-benzyl-N-[2-(benzylamino)ethyl]amine; N,N-Dibenzylethylendiamine 140-28-3 C16H20N2 详情 详情
(II) 10364 3,4-dibromobutanenitrile C4H5Br2N 详情 详情
(III) 10365 2-(1,4-Dibenzyl-2-piperazinyl)acetonitrile C20H23N3 详情 详情
(IV) 10366 2-(1,4-Dibenzyl-2-piperazinyl)ethylamine; 2-(1,4-Dibenzyl-2-piperazinyl)-1-ethanamine C20H27N3 详情 详情
(VI) 10367 ethyl N-[2-(1,4-dibenzyl-2-piperazinyl)ethyl]carbamate C23H31N3O2 详情 详情
(VII) 10368 ethyl N-[2-(2-piperazinyl)ethyl]carbamate C9H19N3O2 详情 详情
(VIII) 10369 Octahydro-6H-pyrazino[1,2-c]pyrimidin-6-one C7H13N3O 详情 详情
(IX) 10370 2-Methyloctahydro-6H-pyrazino[1,2-c]pyrimidin-6-one C8H15N3O 详情 详情
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