1-benzyl-4-(4-methylbenzyl)-4-piperidinol -Drug Synthesis Database

【结构式】

【分子编号】22169

【品名】1-benzyl-4-(4-methylbenzyl)-4-piperidinol

【CA登记号】

【分子式】C₂₀H₂₅NO

【分子量】295.42464

【元素组成】C 81.31% H 8.53% N 4.74% O 5.42%

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：(IV)

The Grignard reagent (II), prepared form 4-methylbenzyl chloride (I), was condensed to N-benzyl-4-piperidone (III) in cold THF to provide the 4-hydroxy-4-benzylpiperidine (IV). Catalytic hydrogenolysis of the N-benzyl group of (IV) over Pd/C gave piperidine (V), which was then alkylated with 2-(4-benzyloxyphenoxy)ethyl bromide (VI) in refluxing acetonitrile to afford (VII). The O-benzyl group of (VII) was finally cleaved by hydrogenolysis in the presence of Pd(OH)2 to furnish the target compound.

参考文献中间体

合成目标

【1】 Zhou, Z.-L.; et al.; Synthesis and SAR of 4-benzyl-4-hydroxy-N-(hydroxy. 216th ACS Natl Meet (Aug. 23-27, Boston) 1998, Abst MEDI 114.

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)	22166	1-(chloromethyl)-4-methylbenzene	104-82-5	C₈H₉Cl	详情	详情
(II)	22167	chloro(4-methylbenzyl)magnesium		C₈H₉ClMg	详情	详情
(III)	15720	1-benzyltetrahydro-4(1H)-pyridinone; 1-Benzyl-4-piperidone; N-Benzyl-4-piperidone; 1-(benzyl)-4-piperidinone; 1-benzylpiperidin-4-one; 1-(benzyl)piperidin-4-one	3612-20-2	C₁₂H₁₅NO	详情	详情
(IV)	22169	1-benzyl-4-(4-methylbenzyl)-4-piperidinol		C₂₀H₂₅NO	详情	详情
(V)	22170	4-(4-methylbenzyl)-4-piperidinol		C₁₃H₁₉NO	详情	详情
(VI)	22171	1-(benzyloxy)-4-(2-bromoethoxy)benzene; benzyl 4-(2-bromoethoxy)phenyl ether		C₁₅H₁₅BrO₂	详情	详情
(VII)	22172	1-[2-[4-(benzyloxy)phenoxy]ethyl]-4-(4-methylbenzyl)-4-piperidinol		C₂₈H₃₃NO₃	详情	详情

Extended Information