[4-(hydroxymethyl)-1-piperidinyl](phenyl)methanone -Drug Synthesis Database

【结构式】

【分子编号】31734

【品名】[4-(hydroxymethyl)-1-piperidinyl](phenyl)methanone

【CA登记号】

【分子式】C₁₃H₁₇NO₂

【分子量】219.28352

【元素组成】C 71.21% H 7.81% N 6.39% O 14.59%

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)

Condensation of ethyl 4-piperidinecarboxylate (I) with benzoyl chloride in pyridine afforded the corresponding benzamide (II). After reduction of the ester group of (II) with NaBH4, the resulting alcohol (III) was converted to chloride (IV) by means of SOCl2. Elimination of the chlorine atom of (IV) with potassium tert-butoxide produced N-benzoyl-4-methylenepiperidine (V), which was hydrolyzed with KOH to yield 4-methylenepiperidine (VI). Finally, condensation of (VI) with the known epoxide (VII) in refluxing EtOH furnished the title compound.

参考文献中间体

合成目标

【1】 Ogura, H.; et al.; Synthesis and antifungal activities of (2R,3R)-2-aryl-1-azolyl-3-(substituted amino)-2-butanol derivatives as topical antifungal agents. Chem Pharm Bull 1999, 47, 10, 1417.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
	10463	Benzoyl chloride	98-88-4	C₇H₅ClO	详情	详情
(I)	17410	Ethyl isonipecotate; ethyl 4-piperidinecarboxylate	1126-09-6	C₈H₁₅NO₂	详情	详情
(II)	31733	ethyl 1-benzoyl-4-piperidinecarboxylate		C₁₅H₁₉NO₃	详情	详情
(III)	31734	[4-(hydroxymethyl)-1-piperidinyl](phenyl)methanone		C₁₃H₁₇NO₂	详情	详情
(IV)	31735	[4-(chloromethyl)-1-piperidinyl](phenyl)methanone		C₁₃H₁₆ClNO	详情	详情
(V)	31736	(4-methylene-1-piperidinyl)(phenyl)methanone		C₁₃H₁₅NO	详情	详情
(VI)	31737	4-methylenepiperidine		C₆H₁₁N	详情	详情
(VII)	31738	1-[[(2R,3S)-2-(2,4-difluorophenyl)-3-methyloxiranyl]methyl]-1H-1,2,4-triazole		C₁₂H₁₁F₂N₃O	详情	详情

Extended Information