• English
  • 简体中文
Login Register
Current Location: Home > Feedback Help Print

【结 构 式】

【分子编号】18346

【品名】ethyl 1-(2,4-dichlorobenzyl)-4-trityl-2-piperazinecarboxylate

【CA登记号】

【 分 子 式 】C33H32Cl2N2O2

【 分 子 量 】559.53476

【元素组成】C 70.84% H 5.76% Cl 12.67% N 5.01% O 5.72%

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)

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
Extended Information