N-(4-nitrobenzyl)-N-tetrahydro-2H-pyran-4-ylamine; N-(4-nitrobenzyl)tetrahydro-2H-pyran-4-amine -Drug Synthesis Database

【结构式】

【分子编号】31564

【品名】N-(4-nitrobenzyl)-N-tetrahydro-2H-pyran-4-ylamine; N-(4-nitrobenzyl)tetrahydro-2H-pyran-4-amine

【CA登记号】

【分子式】C₁₂H₁₆N₂O₃

【分子量】236.27072

【元素组成】C 61% H 6.83% N 11.86% O 20.31%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号：(XII)

Reductive condensation of p-nitrobenzylamine (X) with tetrahydropyran-4-one (XI) in the presence of sodium triacetoxyborohydride gave the tetrahydropyranylamine (XII), and further reductive condensation with formaldehyde afforded the tertiary amine (XIII). Reduction of the nitro group of (XIII) with iron in acetic acid yielded aniline (XIV), which was coupled with acid chloride (IX) to give amide (XV). Quaternization of (XV) with methyl iodide in DMF produced the ammonium iodide (XVI). This was finally converted to the title chloride salt employing an ion exchange resin.

参考文献中间体

合成目标

【1】 Kitayoshi, T.; Aramaki, Y.; Oda, T.; Honda, S.; Shiraishi, M. (Takeda Chemical Industries, Ltd.); Anilide deriv., production and use thereof. JP 1999263764; WO 9932468 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(IX)	31561	2-(4-methylphenyl)-6,7-dihydro-5H-benzo[a]cycloheptene-8-carbonyl chloride		C₁₉H₁₇ClO	详情	详情
(X)	31562	(4-nitrophenyl)methanamine; 4-nitrobenzylamine		C₇H₈N₂O₂	详情	详情
(XI)	31563	tetrahydro-4H-pyran-4-one	29943-42-8	C₅H₈O₂	详情	详情
(XII)	31564	N-(4-nitrobenzyl)-N-tetrahydro-2H-pyran-4-ylamine; N-(4-nitrobenzyl)tetrahydro-2H-pyran-4-amine		C₁₂H₁₆N₂O₃	详情	详情
(XIII)	31565	N-methyl-N-(4-nitrobenzyl)tetrahydro-2H-pyran-4-amine; N-methyl-N-(4-nitrobenzyl)-N-tetrahydro-2H-pyran-4-ylamine		C₁₃H₁₈N₂O₃	详情	详情
(XIV)	31566	N-(4-aminobenzyl)-N-methyltetrahydro-2H-pyran-4-amine; N-(4-aminobenzyl)-N-methyl-N-tetrahydro-2H-pyran-4-ylamine		C₁₃H₂₀N₂O	详情	详情
(XV)	31567	2-(4-methylphenyl)-N-(4-[[methyl(tetrahydro-2H-pyran-4-yl)amino]methyl]phenyl)-6,7-dihydro-5H-benzo[a]cycloheptene-8-carboxamide		C₃₂H₃₆N₂O₂	详情	详情
(XVI)	31568	N,N-dimethyl-N-[4-([[2-(4-methylphenyl)-6,7-dihydro-5H-benzo[a]cyclohepten-8-yl]carbonyl]amino)benzyl]tetrahydro-2H-pyran-4-aminium iodide		C₃₃H₃₉IN₂O₂	详情	详情

Extended Information