1,2,3,4-tetrahydro-1-naphthalenecarbonyl chloride -Drug Synthesis Database

【结构式】

【分子编号】27373

【品名】1,2,3,4-tetrahydro-1-naphthalenecarbonyl chloride

【CA登记号】

【分子式】C₁₁H₁₁ClO

【分子量】194.66044

【元素组成】C 67.87% H 5.7% Cl 18.21% O 8.22%

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)

4-(4-isopropylpiperazinocarbonyl)phenol (IV) is obtained by reaction of 1-isopropylpiperazine (I) and 4-ethoxycarbonyloxybenzoylchloride (II) in CHCl3 using triethylamine (Et3N) as a proton scavenger, followed by removing its ethoxycarbonyl group using pyrrolidine in ethylacetate. Also, the reaction in CHCl3 of 1,2,3,4-tetrahydro-1-naphtoyl chloride (III) and (IV) using Et3N, followed by neutralization of the medium using NaOH and by salt formation using CH3SO3H in ethanol, yields FK-448.

参考文献中间体

合成目标

【1】 Fujii, S.; Hattori, E.; Hirata, M.; Watanabe, K.; Onogi, K.; Nagakura, M. (Kowa Co., Ltd.); Benzoylpiperazine esters and a process for their production. EP 0098713; JP 83225080; US 4898876 .
【2】 Prous, J.; Castaner, J.; FK-448. Drugs Fut 1986, 11, 3, 185.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(A)	11376	Pyrrolidine	123-75-1	C₄H₉N	详情	详情
(I)	27370	1-isopropylpiperazine		C₇H₁₆N₂	详情	详情
(II)	27371	4-(chlorocarbonyl)phenyl ethyl carbonate		C₁₀H₉ClO₄	详情	详情
(III)	27373	1,2,3,4-tetrahydro-1-naphthalenecarbonyl chloride		C₁₁H₁₁ClO	详情	详情
(IV)	27372	(4-hydroxyphenyl)(4-isopropyl-1-piperazinyl)methanone		C₁₄H₂₀N₂O₂	详情	详情

合成路线2

该中间体在本合成路线中的序号：(II)

参考文献中间体

合成目标

【1】 Robinson JR, Kowalczyk JC. 1996. Process for preparing 2-(l-azabicyclo[2, 2, 2] oct-3-yl)-2,3,3a,4, 5,6-hexahydnrlH-benz [de] isoqui nolin-l-one. US 5510486
【1】 Robinson JR, Kowalczyk JC. 1996. Process for preparing 2-(l-azabicyclo[2. 2, 2] oct-3-yl)-2,3,3a,4,5,6-hexahydnrlH-benz [de] isoqui nolin-l-one. US 5510486

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)	16982	1H,3H-benzo[de]isochromene-1,3-dione; 1,8-Naphthalic Anhydride	81-84-5	C₁₂H₆O₃	详情	详情
(I)	66567	1,2,3,4-tetrahydro-1-naphthoic acid	1914-65-4	C₁₁H₁₂O₂	详情	详情
(II)	16985	2-[(3S)-1-azabicyclo[2.2.2]oct-3-yl]-1H-benzo[de]isoquinoline-1,3(2H)-dione		C₁₉H₁₈N₂O₂	详情	详情
(II)	27373	1,2,3,4-tetrahydro-1-naphthalenecarbonyl chloride		C₁₁H₁₁ClO	详情	详情
(III)	16986	2-[(3S)-1-azabicyclo[2.2.2]oct-3-yl]-3-hydroxy-2,3,3a,4,5,6-hexahydro-1H-benzo[de]isoquinolin-1-one		C₁₉H₂₄N₂O₂	详情	详情
(III)	16991	N-[(3S)-1-azabicyclo[2.2.2]oct-3-yl]-5,6,7,8-tetrahydro-1-naphthalenecarboxamide	135729-78-1	C₁₈H₂₄N₂O	详情	详情
(IV)	16987	2-[(3S)-1-azabicyclo[2.2.2]oct-3-yl]-2,4,5,6-tetrahydro-1H-benzo[de]isoquinolin-1-one		C₁₉H₂₂N₂O	详情	详情
(IV)	66568	(2S)-N-((1,2,3,4-tetrahydronaphthalen-1-yl)methyl)quinuclidin-2-amine		C₁₈H₂₆N₂	详情	详情

Extended Information