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【结 构 式】 
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【分子编号】34818 【品名】1-chloroethyl 4-(5-methyl-2-oxo-4-phenyl-2,3-dihydro-1H-imidazol-1-yl)-1-piperidinecarboxylate 【CA登记号】 |
【 分 子 式 】C18H22ClN3O3 【 分 子 量 】363.8438 【元素组成】C 59.42% H 6.09% Cl 9.74% N 11.55% O 13.19% |
合成路线1
该中间体在本合成路线中的序号：(XI)Aminopiperidine (I) was alkylated with 2-bromopropiophenone (VII), and the resulting unstable aminoketone (VIII) was treated with benzoyl isocyanate to produce the benzoyl urea (IX). Cyclization of (IX), followed by benzoyl group cleavage upon treatment with methanolic NaOMe gave the hydroxy imidazolinone (X). This was dehydrated to the imidazolone (V) by means of trifluoroacetic acid. The intermediate (V) was debenzylated to (XII) by reaction with 1-chloroethyl chloroformate, followed by treatment of the resulting (1-chloroethyl) carbamate (XI) with boiling MeOH. The debenzylated piperidine (XII) was finally alkylated with alpha-bromo-m-tolunitrile (XIII) to give the target m-cyanobenzyl derivative.
| 【1】 Carling, R.W.; Moyes, C.R.; Moore, K.W.; et al.; 1-(3-Cyanobenzylpiperidin-4-yl)-5-methyl-4-phenyl-1, 3-dihydroimidazol-2-one: A selective high-affinity antagonist for the human dopamine D(4) receptor with excellent selectivity over ion channels. J Med Chem 1999, 42, 14, 2706. |
| 【2】 Carling, W.R.; Moore, K.W. (Merck Sharp & Dohme Ltd.); Imidazolone and oxazolone derivs. as dopamine antagonists. EP 0719264; JP 1997504272; US 5698573; WO 9507904 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| 22014 | 1-chloro-1-[(chlorocarbonyl)oxy]ethane | 50893-53-3 | C3H4Cl2O2 | 详情 | 详情 | |
| 40601 | benzoyl isocyanate | 4461-33-0 | C8H5NO2 | 详情 | 详情 | |
| (I) | 34808 | 1-Benzyl-4-piperidinylamine; 1-Benzyl-4-piperidinamine; 4-Amino-1-benzylpiperidine | 50541-93-0 | C12H18N2 | 详情 | 详情 |
| (V) | 34812 | 1-(1-benzyl-4-piperidinyl)-5-methyl-4-phenyl-1,3-dihydro-2H-imidazol-2-one | C22H25N3O | 详情 | 详情 | |
| (VII) | 34814 | 2-bromo-1-phenyl-1-propanone | 2114-00-3 | C9H9BrO | 详情 | 详情 |
| (VIII) | 34815 | 2-[(1-benzyl-4-piperidinyl)amino]-1-phenyl-1-propanone | C21H26N2O | 详情 | 详情 | |
| (IX) | 34816 | N'-benzoyl-N-(1-benzyl-4-piperidinyl)-N-(1-methyl-2-oxo-2-phenylethyl)urea | C29H31N3O3 | 详情 | 详情 | |
| (X) | 34817 | 1-(1-benzyl-4-piperidinyl)-4-hydroxy-5-methyl-4-phenyl-2-imidazolidinone | C22H27N3O2 | 详情 | 详情 | |
| (XI) | 34818 | 1-chloroethyl 4-(5-methyl-2-oxo-4-phenyl-2,3-dihydro-1H-imidazol-1-yl)-1-piperidinecarboxylate | C18H22ClN3O3 | 详情 | 详情 | |
| (XII) | 34819 | 5-methyl-4-phenyl-1-(4-piperidinyl)-1,3-dihydro-2H-imidazol-2-one | C15H19N3O | 详情 | 详情 | |
| (XIII) | 13244 | alpha-Bromo-m-tolunitrile; 3-(Bromomethyl)benzonitrile | 28188-41-2 | C8H6BrN | 详情 | 详情 |