[1-[(3,5-dimethoxy-2,5-cyclohexadien-1-yl)methyl]-4-piperidinyl](4-fluorophenyl)methanone -Drug Synthesis Database

【结构式】

【分子编号】51417

【品名】[1-[(3,5-dimethoxy-2,5-cyclohexadien-1-yl)methyl]-4-piperidinyl](4-fluorophenyl)methanone

【CA登记号】

【分子式】C₂₁H₂₆FNO₃

【分子量】359.4407832

【元素组成】C 70.17% H 7.29% F 5.29% N 3.9% O 13.35%

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：(V)

The condensation of 3,5-dimethoxybenzoic acid (I) with 4-(4-fluorobenzoyl)piperidine (II) by means of DCC and HOBT in DMF gives the piperidide (III), which is reduced with LiAlH4 in THF to yield 1-(3,5-dimethoxybenzyl)-4-(4-fluorobenzoyl)piperidine (IV). The reduction of (IV) with Li in liquid ammonia affords the 1,4-dihydro derivative (V), which is finally cyclized with phenylhydrazine (VI) in refluxing aqueous sulfuric acid to provide the target tetrahydrocarbazolone.

参考文献中间体

合成目标

【1】 Masaguer, C.F.; Loza, M.I.; Fontenla, J.A.; Brea, J.; Raviña, E.; Tristan, H.; Butyrophenone analogues in the carbazole series as potential atypical antipsychotics: Synthesis and determination of affinities at D2, 5-HT2A, 5-HT2B and 5-HT2C receptors. Eur J Med Chem 2000, 35, 1, 83.

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)	22761	3,5-dimethoxybenzoic acid	1132-21-4	C₉H₁₀O₄	详情	详情
(II)	21497	(4-Fluorophenyl)(4-piperidinyl)methanone; 4-(4-Fluorobenzoyl)piperidine; 4-(p-Fluorobenzoyl)piperidine	56346-57-7	C₁₂H₁₄FNO	详情	详情
(III)	51415	(3,5-dimethoxyphenyl)[4-(4-fluorobenzoyl)-1-piperidinyl]methanone		C₂₁H₂₂FNO₄	详情	详情
(IV)	51416	[1-(3,5-dimethoxybenzyl)-4-piperidinyl](4-fluorophenyl)methanone		C₂₁H₂₄FNO₃	详情	详情
(V)	51417	[1-[(3,5-dimethoxy-2,5-cyclohexadien-1-yl)methyl]-4-piperidinyl](4-fluorophenyl)methanone		C₂₁H₂₆FNO₃	详情	详情
(VI)	11818	Phenyl hydrazine; 1-Phenylhydrazine	100-63-0	C₆H₈N₂	详情	详情

Extended Information