1-(3-phenylpropyl)piperazine -Drug Synthesis Database

【结构式】

【分子编号】38636

【品名】1-(3-phenylpropyl)piperazine

【CA登记号】

【分子式】C₁₃H₂₀N₂

【分子量】204.31528

【元素组成】C 76.42% H 9.87% N 13.71%

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：(III)

1-(3-Phenylpropyl)piperazine (III) has been obtained by condensation of 3-phenylpropyl bromide (I) with piperazine (II) in refluxing acetonitrile. The condensation of bis(4-fluorophenyl)methanol (IV) with 2-chloroethanol (V) by means of sulfuric acid gives the 2-chloroethyl bis(4-fluorophenyl)methyl ether (VI), which si treated with NaI to yield the corresponding iodo derivative (VII). Finally this compound is condensed with the intermediate piperazine (III) by means of aq. Na2CO3 to afford the target disubstituted piperazine.

参考文献中间体

合成目标

【1】 Zhang, J.; Ironside, M.D.; Sugathapala, P.M.; Robertson, J.; Darey, M.C.P.; Scale-up synthesis of the dopamine uptake inhibitor GBR-12909. Org Process Res Dev 2002, 6, 5, 621.

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)	20884	1-(3-bromopropyl)benzene	637-59-2	C₉H₁₁Br	详情	详情
(II)	10355	Diethylenediamine; Piperazine	110-85-0	C₄H₁₀N₂	详情	详情
(III)	38636	1-(3-phenylpropyl)piperazine		C₁₃H₂₀N₂	详情	详情
(IV)	41974	4,4'-Difluorobenzhydrol; bis(4-Fluorophenyl)methanol; alpha-(4-fluorophenyl)benzenemethanol; 4-fluoro-alpha-(4-fluorophenyl)benzenemethanol	365-24-2	C₁₃H₁₀F₂O	详情	详情
(V)	10384	2-Chloro-1-ethanol; Ethylene chlorohydrin	107-07-3	C₂H₅ClO	详情	详情
(VI)	54931	1-[(2-chloroethoxy)(4-fluorophenyl)methyl]-4-fluorobenzene; bis(4-fluorophenyl)methyl 2-chloroethyl ether		C₁₅H₁₃ClF₂O	详情	详情
(VII)	56868	bis(4-fluorophenyl)methyl 2-iodoethyl ether; 1-fluoro-4-[(4-fluorophenyl)(2-iodoethoxy)methyl]benzene		C₁₅H₁₃F₂IO	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 cyclization of pyridine-3-carbaldehyde (I) with L-cysteine (II) gives 2-(3-pyridyl)thiazolidine-4(R)-carboxylic acid (II), which is finally condensed with 1-(3-phenylpropyl)piperazine (IV) by means of DCC and HOBT in DMF. The intermediate 1-(3-phenylpropyl)piperazine (IV) has been obtained as follows: The condensation of piperazine-1-carboxylic acid ethyl ester (V) with 3-phenylpropyl bromide (VI) by means of K2CO3 in 2-butanone gives 4-(3-phenylpropyl)piperazine-1-carboxylic acid ethyl ester (VII), which is decarboxylated with NaOH in refluxing ethanol.

参考文献中间体

合成目标

【1】 Mase, T.; Hara, H.; Nagaoka, H.; Takahasi, T.; Suzuki, T.; Tomioka, K.; Yamada, T. (Yamanouchi Pharmaceutical Co., Ltd.); Saturated heterocyclic carboxamide derivs.. AU 8812080; EP 0279681; JP 1988208582; US 4987132 .

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)	12849	Nicotinaldehyde; 3-Pyridinecarboxaldehyde	500-22-1	C₆H₅NO	详情	详情
(II)	38633	(2S)-2-amino-2-(methylsulfanyl)ethanoic acid		C₃H₇NO₂S	详情	详情
(III)	38634	(4R)-2-(3-pyridinyl)-1,3-thiazolidine-4-carboxylic acid		C₉H₁₀N₂O₂S	详情	详情
(IV)	38636	1-(3-phenylpropyl)piperazine		C₁₃H₂₀N₂	详情	详情
(V)	24694	N-ethoxycarbonylpiperidine; Ethyl 1-piperazinecarboxylate; N-Ethoxycarbonyl piperazine; N-Carbethoxy piperazine	120-43-4	C₇H₁₄N₂O₂	详情	详情
(VI)	20884	1-(3-bromopropyl)benzene	637-59-2	C₉H₁₁Br	详情	详情
(VII)	38635	ethyl 4-(3-phenylpropyl)-1-piperazinecarboxylate		C₁₆H₂₄N₂O₂	详情	详情

Extended Information