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 -Drug Synthesis Database

【结构式】

【分子编号】60704

【品名】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

【CA登记号】

【分子式】C₂₃H₃₀FN₃O₂

【分子量】399.5086232

【元素组成】C 69.15% H 7.57% F 4.76% N 10.52% O 8.01%

与该中间体有关的原料药合成路线共 3 条

合成路线1 合成路线2 合成路线3

合成路线1

该中间体在本合成路线中的序号：(VII)

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：(VII)

The reaction of o-phenylenediamine (IX) with 4-chloropyridine (VIII) gives 2-(4-pyridylamino)aniline (X), which is condensed with 2-(3-chloropropyl)-2-(4-fluorophenyl)-1,3-dioxolane (I) to give the corresponding pyridinium salt (XI). The reduction of (XI) with NaBH4 yields 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
(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
(VIII)	32889	4-chloropyridine	7379-35-3	C₅H₄ClN	详情	详情
(IX)	12824	2-Aminophenylamine; o-Phenylenediamine; 1,2-Benzenediamine	95-54-5	C₆H₈N₂	详情	详情
(X)	60705	N-(2-aminophenyl)-N-(4-pyridinyl)amine; N~1~-(4-pyridinyl)-1,2-benzenediamine		C₁₁H₁₁N₃	详情	详情
(XI)	60706	4-(2-aminoanilino)-1-{3-[2-(4-fluorophenyl)-1,3-dioxolan-2-yl]propyl}pyridinium chloride		C₂₃H₂₅ClFN₃O₂	详情	详情

合成路线3

该中间体在本合成路线中的序号：(V)

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