2-Benzoylpyridine; Phenyl(2-pyridinyl)methanone -Drug Synthesis Database

【结构式】

【分子编号】32233

【品名】2-Benzoylpyridine; Phenyl(2-pyridinyl)methanone

【CA登记号】91-02-1

【分子式】C₁₂H₉NO

【分子量】183.2096

【元素组成】C 78.67% H 4.95% N 7.65% O 8.73%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(X)

The reaction of dimethylpiperidine (IV) with 3-bromopropanol (VII) in refluxing xylene gives 1-(3-hydroxypropyl)-2,6-cis-dimethylpiperidine (VIII), which by treatment with SOCl2 in refluxing benzene is converted into 1-(3-chloropropyl)-2,6-cis-dimethylpiperidine (IX). Finally, this compound is condensed with 2-benzoylpyridine (X) by means of Li in THF.

参考文献中间体

合成目标

【1】 Fleming, R.W. (Pfizer Inc.); Antiarrhythmic (+,-)-cis- alpha [3-(2,6-dimethyl-1-piperidinyl)propyl]-alpha-phenyl-2-pyridinemethanols. US 4112103 .
【2】 Blancafort, P.; Serradell, M.N.; Castaner, J.; Hillier, K.; Pirmenol hydrochloride. Drugs Fut 1981, 6, 4, 234.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(IV)	32229	(2R,6S)-2,6-dimethylpiperidine; cis-2,6-dimethylpiperidine		C₇H₁₅N	详情	详情
(VII)	12573	3-Bromo-1-propanol; 3-Bromopropanol	627-18-9	C₃H₇BrO	详情	详情
(VIII)	32231	1-(3-hydroxypropyl)-2,6-cis-dimethylpiperidine; 3-[(2R,6S)-2,6-dimethylpiperidinyl]-1-propanol		C₁₀H₂₁NO	详情	详情
(IX)	32232	1-(3-chloropropyl)-2,6-cis-dimethylpiperidine; (2R,6S)-1-(3-chloropropyl)-2,6-dimethylpiperidine		C₁₀H₂₀ClN	详情	详情
(X)	32233	2-Benzoylpyridine; Phenyl(2-pyridinyl)methanone	91-02-1	C₁₂H₉NO	详情	详情

合成路线2

该中间体在本合成路线中的序号：(I)

This compound can be obtained by two related ways: 1) The Wittig condensation of 2-benzoylpyridine (I) with diethyl cyanomethylphosphonate (II) by means of sodium ethoxide in hot ethanol gives 3-phenyl-3-(2-pyridyl)acrylonitrite (III), which is reduced with NaBH4 in refluxing ethanol to yield 3-phenyl-3-(2-pyridyl)propionitrite (IV). Finally, this compound is cyclized with ethylenediamine (V) at reflux temperature. 2) The cyctization of 3-phenyl-3-(2-pyridyl)acrylonitrite (III) with ethylenediamine (V) at reflux temperature gives 2-[2-phenyl-2-(2-pyridyl)viny]-2-imidazoline (VI), which is then reduced with H2 over Pd/C in ethanol.

参考文献中间体

合成目标

【1】 Ishikawa, F.; Cyclic guanidines. X. Synthesis of 2-(2,2-disubstituted ethenyl- and ethyl)-2-imidazolines as potent hypoglycemics. Chem Pharm Bull 1980, 28, 5, 1394-1402.
【2】 Castaner, J.; Hillier, K.; Blancafort, P.; Serradell, M.N.; DG-5128. Drugs Fut 1982, 7, 8, 550.

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)	32233	2-Benzoylpyridine; Phenyl(2-pyridinyl)methanone	91-02-1	C₁₂H₉NO	详情	详情
(II)	10045	Diethyl cyanomethylphosphonate	2537-48-6	C₆H₁₂NO₃P	详情	详情
(III)	37098	(E)-3-phenyl-3-(2-pyridinyl)-2-propenenitrile		C₁₄H₁₀N₂	详情	详情
(IV)	37100	3-phenyl-3-(2-pyridinyl)propanenitrile		C₁₄H₁₂N₂	详情	详情
(V)	14754	ethylenediamine;1,2-Diaminoethane;ethane-1,2-diamine；1,2-Ethanediamine	107-15-3	C₂H₈N₂	详情	详情
(VI)	37099	2-[(E)-2-(4,5-dihydro-1H-imidazol-2-yl)-1-phenylethenyl]pyridine		C₁₆H₁₅N₃	详情	详情

Extended Information