1,2,3,4-tetrahydrospiro[isoquinoline-1,4'-piperidin]-3-one -Drug Synthesis Database

【结构式】

【分子编号】25126

【品名】1,2,3,4-tetrahydrospiro[isoquinoline-1,4'-piperidin]-3-one

【CA登记号】

【分子式】C₁₃H₁₆N₂O

【分子量】216.28292

【元素组成】C 72.19% H 7.46% N 12.95% O 7.4%

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)

The known piperidinoethanol derivative (I) was converted to the mesylate (II) upon treatment with methanesulfonyl chloride and triethylamine. Displacement of the mesylate group of (II) with the spiro-substituted piperidine (III) provided adduct (IV). Finally, quaternization of piperidine (IV) with iodomethane gave the corresponding ammonium salt as a mixture of cis/trans isomers that were separated by column chromatography.

参考文献中间体

合成目标

【1】 Kubota, H.; Okamoto, Y.; Fujii, M.; Ikeda, K.; Takeuchi, M.; Shibanuma, T.; Isomura, Y.; Synthesis and NK1 receptor antagonistic activity of (±)-1-acyl-3-(3,4-dichlorophenyl)-3-[2-(spiro-substituted piperidin-1'-yl)ethyl]piperidines. Bioorg Med Chem Lett 1998, 8, 12, 1541.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	51324	1-[3-(3,4-dichlorophenyl)-3-(2-hydroxyethyl)-1-piperidinyl]-2-(3-isopropoxyphenyl)-1-ethanone	C₂₄H₂₉Cl₂NO₃	详情	详情
(II)	51325	2-[3-(3,4-dichlorophenyl)-1-[2-(3-isopropoxyphenyl)acetyl]-3-piperidinyl]ethyl methanesulfonate	C₂₅H₃₁Cl₂NO₅S	详情	详情
(III)	25126	1,2,3,4-tetrahydrospiro[isoquinoline-1,4'-piperidin]-3-one	C₁₃H₁₆N₂O	详情	详情
(IV)	51326		C₃₇H₄₃Cl₂N₃O₃	详情	详情

合成路线2

该中间体在本合成路线中的序号：(III)

Treatment of alcohol (I) with methanesulfonyl chloride in the presence of triethylamine provided mesylate (II), which was condensed with the spirosubstituted piperidine (III) to give the desired compound.

参考文献中间体

合成目标

【1】 Kubota, H.; Kakefuda, A.; Okamoto, Y.; Fujii, M.; Yamamoto, O.; Yamagiwa, Y.; Orita, M.; Ikeda, K.; Takeuchi, M.; Shibanuma, T.; Isomura, Y.; Spiro-substituted piperidines as neurokinin receptor antagonists. III. Synthesis of (±)-N-[2-(3,4-dichlorophenyl)-4-(spiro-substituted piperidin-1'-yl)butyl]-N-methylbenzamides and evaluation of NK1-NK2 dual antagonistic activities. Chem Pharm Bull 1998, 46, 10, 1538.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	25124	N-[2-(3,4-dichlorophenyl)-4-hydroxybutyl]-3,4,5-trimethoxy-N-methylbenzamide	C₂₁H₂₅Cl₂NO₅	详情	详情
(II)	25125	3-(3,4-dichlorophenyl)-4-[methyl(3,4,5-trimethoxybenzoyl)amino]butyl methanesulfonate	C₂₂H₂₇Cl₂NO₇S	详情	详情
(III)	25126	1,2,3,4-tetrahydrospiro[isoquinoline-1,4'-piperidin]-3-one	C₁₃H₁₆N₂O	详情	详情

Extended Information