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【结 构 式】 
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【分子编号】18348 【品名】ethyl 1-(2,4-dichlorobenzyl)-4-methyl-2-piperazinecarboxylate 【CA登记号】 |
【 分 子 式 】C15H20Cl2N2O2 【 分 子 量 】331.24148 【元素组成】C 54.39% H 6.09% Cl 21.41% N 8.46% O 9.66% |
合成路线1
该中间体在本合成路线中的序号：(IX)Condensation of N,N'-dibenzylethylenediamine (I) with ethyl 2,3-dibromopropionate (II) in the presence of Et3N in toluene at 80 C gave, after acidification, piperazine (III). Then, hydrogenolytic N-debenzylation in the presence of Pd/C provided ethyl piperazine-2-carboxylate (IV), which was selectively alkylated at position 4 with 1 equivalent of triphenylmethyl chloride in the presence of Et3N at -10 C to give (V). Subsequent alkylation with 2,4-dichlorobenzyl chloride (VI) in the presence of K2CO3 and a catalytic amount of KI provided (VII). Removal of the N-trityl group by treatment with HCl in either acetone or ethanol afforded piperarine (VIII), which was N-methylated by reaction with formaldehyde and formic acid in refluxing MeOH. Finally, the resulting compound (IX) was converted into the imidazoline on treatment with ethylenediamine and trimethylaluminum in refluxing toluene.
| 【1】 Rondu, F.; et al.; Design and synthesis of imidazoline derivatives active on glucose homeostasis in a rat model of type II diabetes. 1. Synthesis and biological activities of N-benzyl-N'-(arylalkyl)-2-(4', 5'-dihydro-1'H-imidazol-2'-yl)piperazines. J Med Chem 1997, 40, 23, 3793. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| 14754 | ethylenediamine;1,2-Diaminoethane;ethane-1,2-diamine；1,2-Ethanediamine | 107-15-3 | C2H8N2 | 详情 | 详情 | |
| (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) | 18341 | ethyl 2,3-dibromopropanoate | 3674-13-3 | C5H8Br2O2 | 详情 | 详情 |
| (III) | 18342 | ethyl 1,4-dibenzyl-2-piperazinecarboxylate | 72351-59-8 | C21H26N2O2 | 详情 | 详情 |
| (IV) | 18343 | ethyl 2-piperazinecarboxylate | 89941-07-1 | C7H14N2O2 | 详情 | 详情 |
| (V) | 18344 | ethyl 4-trityl-2-piperazinecarboxylate | C26H28N2O2 | 详情 | 详情 | |
| (VI) | 18345 | 2,4-Dichlorobenzyl chloride; 2,4-Dichloro-1-(chloromethyl)benzene | 94-99-5 | C7H5Cl3 | 详情 | 详情 |
| (VII) | 18346 | ethyl 1-(2,4-dichlorobenzyl)-4-trityl-2-piperazinecarboxylate | C33H32Cl2N2O2 | 详情 | 详情 | |
| (VIII) | 18347 | ethyl 1-(2,4-dichlorobenzyl)-2-piperazinecarboxylate | C14H18Cl2N2O2 | 详情 | 详情 | |
| (IX) | 18348 | ethyl 1-(2,4-dichlorobenzyl)-4-methyl-2-piperazinecarboxylate | C15H20Cl2N2O2 | 详情 | 详情 |