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【结 构 式】

【分子编号】15289

【品名】4-oxo-2-phenyl-2-(2-pyridinyl)pentanenitrile

【CA登记号】

【 分 子 式 】C16H14N2O

【 分 子 量 】250.30004

【元素组成】C 76.78% H 5.64% N 11.19% O 6.39%

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:(III)

Vamicamide is synthesized by two closely related ways (1). Scheme 1: 1) The alkylation of 2-phenyl-2-(2-pyridyl)acetonitrile (I) with chloroacetone (II) is achieved in the presence of KOH in DMSO to give the 4-oxopentanenitrile derivative (III). Compound (III) is then converted to (V) by reaction with dimethylamine (IV) using titanium tetrachloride and successive reduction with NaBH4. The nitrile (V) (a mixture of two diastereoisomers) is hydrolyzed with concentrated H2SO4 in acetic acid to give the final pentanamide derivative as a racemic mixture of two diastereoisomers, A-racemate and B-racemate. Separation is accomplished by recrystallization of their maleic acid salts. The racemates are resolved by recrystallization with (-)-dibenzoyl-L-tartaric acid. 2) The reaction of 2-phenyl-2-(2-pyridyl)acetonitrile (I) with 2-(dimethylamino)propylchloride (VI) using a base affords the intermediate (V), which is hydrolyzed with concentrated sulfuric acid in acetic acid to give the final pentanamide derivative as a mixture of two diastereoisomers. These are resolved by recrystallization.

1 Mealy, N.; Castaner, J.; Vamicamide. Drugs Fut 1995, 20, 10, 1018.
2 Oyasu, H.; Nagano, M.; Akahane, A.; Tomoi, M.; Tada, T.; Matsuo, M.; Synthesis and anticholinergic activity of the four stereoisomers of 4-(dimethylamino)-2-phenyl-2-(2-pyridyl)pentanamide. J Med Chem 1994, 37, 9, 1378-81.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(VI)) 15290 N-(2-chloro-1-methylethyl)-N,N-dimethylamine; 1-chloro-N,N-dimethyl-2-propanamine C5H12ClN 详情 详情
(I) 15287 alpha-phenyl-2-pyridineacetonitrile; 2-phenyl-2-(2-pyridinyl)acetonitrile; 2-Pyridineacetonitrile; Phenyl-2-(2-pyridinyl)acetonitrile 5005-36-7 C13H10N2 详情 详情
(II) 15288 1-Chloroacetone; Chloroacetone 78-95-5 C3H5ClO 详情 详情
(III) 15289 4-oxo-2-phenyl-2-(2-pyridinyl)pentanenitrile C16H14N2O 详情 详情
(V) 15291 4-(dimethylamino)-2-phenyl-2-(2-pyridinyl)pentanenitrile C18H21N3 详情 详情
Extended Information