1-{3-[2-(4-fluorophenyl)-1,3-dioxolan-2-yl]propyl}-N-(2-nitrophenyl)-4-piperidinamine; N-(1-{3-[2-(4-fluorophenyl)-1,3-dioxolan-2-yl]propyl}-4-piperidinyl)-N-(2-nitrophenyl)amine -Drug Synthesis Database

【结构式】

【分子编号】60703

【品名】1-{3-[2-(4-fluorophenyl)-1,3-dioxolan-2-yl]propyl}-N-(2-nitrophenyl)-4-piperidinamine; N-(1-{3-[2-(4-fluorophenyl)-1,3-dioxolan-2-yl]propyl}-4-piperidinyl)-N-(2-nitrophenyl)amine

【CA登记号】

【分子式】C₂₃H₂₈FN₃O₄

【分子量】429.4915432

【元素组成】C 64.32% H 6.57% F 4.42% N 9.78% O 14.9%

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：(VI)

The reaction of 2-(3-chloropropyl)-2-(4-fluorophenyl)-1,3-dioxolane (I) with 4-aminopyridine (II) gives the corresponding pyridinium salt (III), which is reduced with NaBH4 to 2-[3-(4-aminopiperidyl)propyl]-2-(4-fluorophenyl)-1,3-dioxolane (IV). The condensation of (IV) with 2-chloronitrobenzene (V) yields 2-[3-[4-(2-nitroanilino)piperidyl]propyl]-2-(4-fluorophenyl)-1,3-dioxolane (VI), which is hydrogenated with H2 over Raney-Ni affording the corresponding amino compound (VII). Finally this compound is cyclized with carbon disulfide and KOH

参考文献中间体

合成目标

【1】 JP 76095096 .

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)	28203	2-(3-chloropropyl)-2-(4-fluorophenyl)-1,3-dioxolane	3308-94-9	C₁₂H₁₄ClFO₂	详情	详情
(II)	25661	4-pyridinamine; 4-aminopyridine	5044-74-5	C₅H₆N₂	详情	详情
(III)	60701	4-amino-1-{3-[2-(4-fluorophenyl)-1,3-dioxolan-2-yl]propyl}pyridinium chloride		C₁₇H₂₀ClFN₂O₂	详情	详情
(IV)	60702	1-{3-[2-(4-fluorophenyl)-1,3-dioxolan-2-yl]propyl}-4-piperidinamine; 1-{3-[2-(4-fluorophenyl)-1,3-dioxolan-2-yl]propyl}-4-piperidinylamine		C₁₇H₂₅FN₂O₂	详情	详情
(V)	15248	1-chloro-2-nitrobenzene	88-73-3	C₆H₄ClNO₂	详情	详情
(VI)	60703	1-{3-[2-(4-fluorophenyl)-1,3-dioxolan-2-yl]propyl}-N-(2-nitrophenyl)-4-piperidinamine; N-(1-{3-[2-(4-fluorophenyl)-1,3-dioxolan-2-yl]propyl}-4-piperidinyl)-N-(2-nitrophenyl)amine		C₂₃H₂₈FN₃O₄	详情	详情
(VII)	60704	N-(2-aminophenyl)-N-(1-{3-[2-(4-fluorophenyl)-1,3-dioxolan-2-yl]propyl}-4-piperidinyl)amine; N~1~-(1-{3-[2-(4-fluorophenyl)-1,3-dioxolan-2-yl]propyl}-4-piperidinyl)-1,2-benzenediamine		C₂₃H₃₀FN₃O₂	详情	详情

合成路线2

该中间体在本合成路线中的序号：(IV)

The condensation of 4-chloro-1-(4-fluorophenyl)-1-butanone ethylene ketal (I) with 4-(2-nitroanilino)piperidine (III) by means of KI in refluxing butanol gives 1-[3-(4-fluorobenzoyl)propyl]-4-(2-nitroanilino)piperidine ethylene ketal (IV), which is reduced with H2 over Raney-Ni in methanol yielding the corresponding amino compound (V). Finally this compound is cyclized with CS2 by means of KOH in refluxing ethanol

参考文献中间体

合成目标

【1】 Katsujiro, U.; et al. (Daiichi Seiyaku Co., Ltd.); DE 2526393; GB 1467097; US 3963727 .
【2】 Katsujiro, U.; et al. (Daiichi Seiyaku Co., Ltd.); JP 7584579 .
【3】 Katsujiro, U.; et al. (Daiichi Seiyaku Co.; Ltd.); BE 830171; ZA 7593577 .
【4】 Castaner, J.; Blancafort, P.; DD-3480. Drugs Fut 1978, 3, 6, 451.

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)	28203	2-(3-chloropropyl)-2-(4-fluorophenyl)-1,3-dioxolane	3308-94-9	C₁₂H₁₄ClFO₂	详情	详情
(III)	60708	N-(2-nitrophenyl)-4-piperidinamine; N-(2-nitrophenyl)-N-(4-piperidinyl)amine		C₁₁H₁₅N₃O₂	详情	详情
(IV)	60703	1-{3-[2-(4-fluorophenyl)-1,3-dioxolan-2-yl]propyl}-N-(2-nitrophenyl)-4-piperidinamine; N-(1-{3-[2-(4-fluorophenyl)-1,3-dioxolan-2-yl]propyl}-4-piperidinyl)-N-(2-nitrophenyl)amine		C₂₃H₂₈FN₃O₄	详情	详情
(V)	60704	N-(2-aminophenyl)-N-(1-{3-[2-(4-fluorophenyl)-1,3-dioxolan-2-yl]propyl}-4-piperidinyl)amine; N~1~-(1-{3-[2-(4-fluorophenyl)-1,3-dioxolan-2-yl]propyl}-4-piperidinyl)-1,2-benzenediamine		C₂₃H₃₀FN₃O₂	详情	详情

Extended Information