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【结 构 式】

【分子编号】34817

【品名】1-(1-benzyl-4-piperidinyl)-4-hydroxy-5-methyl-4-phenyl-2-imidazolidinone

【CA登记号】

【 分 子 式 】C22H27N3O2

【 分 子 量 】365.4754

【元素组成】C 72.3% H 7.45% N 11.5% O 8.76%

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:(X)

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
Extended Information