【结 构 式】 |
【分子编号】39054 【品名】ethyl 2-[2-[(ethoxycarbonyl)(ethyl)amino]ethyl]-4-methyl-1-piperazinecarboxylate 【CA登记号】 |
【 分 子 式 】C15H29N3O4 【 分 子 量 】315.41308 【元素组成】C 57.12% H 9.27% N 13.32% O 20.29% |
合成路线1
该中间体在本合成路线中的序号:(VIII)Condensation of dimethyl aspartate (II) with benzyloxy carbonyl sarcosine (I) using DCI gave dimethyl benzyloxycarbonyl sarcosylaspartate (III). Removal of benzyloxycarbonyl function from (III) by catalytic hydrogenation or HBr-AcOH followed by cyclization, effected by storage over P2O5 in vacuo for 48 h, gave methyl (1-methyl-2,5-dioxopiperazin-3-yl)acetate (IV). When (IV) was reacted with ethylamine in a sealed tube for 36 h, it yielded N-ethyl-2-(1-methyl-2,5,dioxopiperazin-3-yl)acetamide (V). The compound (V) was reduced with LiAlH4 to give 1-methyl-3-(2-ethylamino)ethylpiperazine (VI). When (VI) was condensed with ethyl chloroformate (A) at pH 3-3.5, a mixture of monocarbamates (VIIa, VIIb) were obtained. Cyclization of the monocarbamates (VIIa, VIIb) were effected by treatment with sodium ethoxide to afford 3-ethyl-8-methyl-1,3,8-triazabicyclo[4.4.0]decan-2-one (centperazine). When (VI) was reacted with ethyl chloroformate (A) in the presence of NaOC2H5 or Et3N, the dicarbamate (VIII) was formed.
【1】 Saxena, R.; et al.; Studies in potential filaricides. 5. 3-Ethyl-8-methyl-1,3,8-triazabicyclo[4.4.0]decan-2-one, a new antifilarial agent. J Med Chem 1971, 14, 10, 929. |
【2】 Arya, V.P.; Centperazine. Drugs Fut 1980, 5, 5, 229. |
中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
---|---|---|---|---|---|---|
(A) | 12229 | (2R,3S)-5,5-Dimethoxy-3-(phenylselanyl)-1,2-pentanediol | C13H20O4Se | 详情 | 详情 | |
(VIIa) | 39052 | ethyl ethyl[2-(4-methyl-2-piperazinyl)ethyl]carbamate | C12H25N3O2 | 详情 | 详情 | |
(VIIb) | 39053 | ethyl 2-[2-(ethylamino)ethyl]-4-methyl-1-piperazinecarboxylate | C12H25N3O2 | 详情 | 详情 | |
(I) | 39046 | (benzyloxy)carbonyl(methyl)carbamic acid | C10H11NO4 | 详情 | 详情 | |
(II) | 39047 | dimethyl 2-aminosuccinate | C6H11NO4 | 详情 | 详情 | |
(III) | 39048 | dimethyl 2-([2-[[(benzyloxy)carbonyl](methyl)amino]acetyl]amino)succinate | C17H22N2O7 | 详情 | 详情 | |
(IV) | 39049 | methyl 2-(4-methyl-3,6-dioxo-2-piperazinyl)acetate | C8H12N2O4 | 详情 | 详情 | |
(V) | 39050 | N-ethyl-2-(4-methyl-3,6-dioxo-2-piperazinyl)acetamide | C9H15N3O3 | 详情 | 详情 | |
(VI) | 39051 | N-ethyl-2-(4-methyl-2-piperazinyl)-1-ethanamine; N-ethyl-N-[2-(4-methyl-2-piperazinyl)ethyl]amine | C9H21N3 | 详情 | 详情 | |
(VIII) | 39054 | ethyl 2-[2-[(ethoxycarbonyl)(ethyl)amino]ethyl]-4-methyl-1-piperazinecarboxylate | C15H29N3O4 | 详情 | 详情 |