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【结 构 式】 
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【分子编号】15244 【品名】1-(4-chlorophenyl)-2-[methyl(2-nitrobenzyl)amino]-1-ethanol 【CA登记号】 |
【 分 子 式 】C16H17ClN2O3 【 分 子 量 】320.77536 【元素组成】C 59.91% H 5.34% Cl 11.05% N 8.73% O 14.96% |
合成路线1
该中间体在本合成路线中的序号：(III)Two related methods have been described: The alkylation of 2-nitrobenzylmethylamine (I) with p-chlorphenyloxyran (II) in boiling ethanol affords N-(2-nitrobenzyl)-2-(methylamino)-1-(4-chlorphenyl)-1-ethanol (III), which is further reduced via NaBH4/NiCl2 in boiling methanol to N-(2-aminobenzyl)-2-(methylamino)-1-(4-chlorphenyl)-1-ethanol (IV). The acylation of (IV) with ethyl chloroformate in the presence of pyridine and in a medium of benzene - DMFA (Method A) results in N-[2-(ethoxycarbonyl)amino]-2-(methylamino)-1-(4-chlorophenyl)-1-ethanol (V). The latter is cyclodehydrated by means of conc.H2SO4 in dichloroethane. According to method B, the amino alcohol (IV) is cyclodehydrated by conc.H2SO4 to 8-amino-4-(4-chlorophenyl)-2-methyl-1,2,3-4-tetrahydroisoquinoline (VI), which is acylated with ethyl chloroformate in boiling benzene.
| 【1】 Ivanova, N.; Ivanov, T.; Mondeshka, D.; Berova, N.; Angelova, I.; Rakovska, R.; Bojadjiev, S.; Tancheva, C.; Tascheva, D.; Synthesis, stereochemistry, and antiulcer activity of 4-phenyltetrahydroisoquinolines. Arch Pharm 1990, 323, 1, 3. |
| 【2】 Ivanova, N.; Angelova, J.; Mondeshka, D.; Ivanov, C.; Gastrophenzine. Drugs Fut 1992, 17, 2, 104. |
| 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) | 15242 | N-methyl(2-nitrophenyl)methanamine; N-methyl-N-(2-nitrobenzyl)amine | C8H10N2O2 | 详情 | 详情 | |
| (II) | 15243 | 2-(4-chlorophenyl)oxirane | C8H7ClO | 详情 | 详情 | |
| (III) | 15244 | 1-(4-chlorophenyl)-2-[methyl(2-nitrobenzyl)amino]-1-ethanol | C16H17ClN2O3 | 详情 | 详情 | |
| (IV) | 15245 | 2-[(2-aminobenzyl)(methyl)amino]-1-(4-chlorophenyl)-1-ethanol | C16H19ClN2O | 详情 | 详情 | |
| (V) | 15246 | ethyl N-(2-[[[2-(4-chlorophenyl)-2-hydroxyethyl](methyl)amino]methyl]phenyl)carbamate | C19H23ClN2O3 | 详情 | 详情 | |
| (VI) | 15247 | 4-(4-chlorophenyl)-2-methyl-1,2,3,4-tetrahydro-8-isoquinolinamine; 4-(4-chlorophenyl)-2-methyl-1,2,3,4-tetrahydro-8-isoquinolinylamine | C16H17ClN2 | 详情 | 详情 |