6-Amino-3,4-dihydro-2H-spiro[1-benzopyran-2,4'-piperidin]-4-one -Drug Synthesis Database

【结构式】

【分子编号】21615

【品名】6-Amino-3,4-dihydro-2H-spiro[1-benzopyran-2,4'-piperidin]-4-one

【CA登记号】

【分子式】C₁₃H₁₆N₂O₂

【分子量】232.28232

【元素组成】C 67.22% H 6.94% N 12.06% O 13.78%

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：(V)

Friedel-Crafts acetylation of acetaminophen (I) using acetyl chloride and AlCl3 gave acetophenone (II). Subsequent condensation of (II) with N-(tert-butoxycarbonyl)-4-piperidone (III) in the presence of pyrrolidine provided the spirochroman-2,4'-piperidine (IV), from which the diamine (V) was obtained by acid hydrolysis. The piperidine amino group of (VI) was then alkylated with 1-(2-bromoethyl)naphthalene (VI) to afford (VII). Finally, condensation of the remaining amino group of (VII) with the sulfonyl chloride (VIII) furnished the title sulfonamide.

参考文献中间体

合成目标

【1】 Nerenberg, J.B.; et al.; 4-Oxospiro[benzopyran-2,4'-piperidines] as selective alpha1a-adrenergic receptor antagonists. Bioorg Med Chem Lett 1999, 9, 2, 291.

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)	21611	4'-Hydroxyacetanilide;4-Acetamidophenol;N-Acetyl-4-aminophenol;Paracetamol;Acetaminophen;p-Hydroxyacetanilide; Paracetamol; N-(4-hydroxyphenyl)acetamide	103-90-2	C₈H₉NO₂	详情	详情
(II)	21612	N-(3-acetyl-4-hydroxyphenyl)acetamide		C₁₀H₁₁NO₃	详情	详情
(III)	18620	tert-butyl 4-oxo-1-piperidinecarboxylate;BOC-Piperidone;N-(tert-Butoxycarbonyl)-4-piperidone; N-Boc-4-piperidone	79099-07-3	C₁₀H₁₇NO₃	详情	详情
(IV)	21614	6-Aceatmido-4-oxo-3,4-dihydro-2H-spiro[1-benzopyran-2,4'-piperidin]-1'-ylcarboxylic acid tert-butyl ester		C₂₀H₂₆N₂O₅	详情	详情
(V)	21615	6-Amino-3,4-dihydro-2H-spiro[1-benzopyran-2,4'-piperidin]-4-one		C₁₃H₁₆N₂O₂	详情	详情
(VI)	21616	1-(2-bromoethyl)naphthalene	13686-49-2	C₁₂H₁₁Br	详情	详情
(VII)	21617	6-Amino-1'-[2-(1-naphthyl)ethyl]-3,4-dihydro-2H-spiro[1-benzopyran-2,4'-piperidin]-4-one		C₂₅H₂₆N₂O₂	详情	详情
(VIII)	21618	3,5-dimethyl-4-isoxazolesulfonyl chloride	80466-79-1	C₅H₆ClNO₃S	详情	详情

Extended Information