1-benzyl-4-[4-(benzyloxy)phenyl]-4-piperidinol -Drug Synthesis Database

【结构式】

【分子编号】43157

【品名】1-benzyl-4-[4-(benzyloxy)phenyl]-4-piperidinol

【CA登记号】

【分子式】C₂₅H₂₇NO₂

【分子量】373.49492

【元素组成】C 80.4% H 7.29% N 3.75% O 8.57%

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：(VI)

In an alternative procedure, lithiation of 4-(benzyloxy)-1-bromobenzene (IV), followed by addition of 1-benzyl-4-piperidone (V), gave piperidinol (VI). Subsequent treatment of (VI) with HCl produced dehydration of the tertiary alcohol and benzyl ether cleavage to give (VII). Double bond reduction and hydrogenolysis of the N-benzyl group of (VII) with H2 over Pd/C gave 4-(4-hydroxyphenyl)piperidine (VIII). This was finally alkylated with tosylate (II) to yield the title compound.

参考文献中间体

合成目标

【1】 Guzikowski, A.P.; Acosta-Burruel, M.; Tamiz, A.P.; et al.; Synthesis of N-substituted 4-(4-hydroxyphenyl)piperidines, 4-(4-hydroxybenzyl)piperidines, and (±)-3-(4-hydroxyphenyl)pyrrolidines: Selective antagonists at the 1A/2B NMDA receptor subtype. J Med Chem 2000, 43, 5, 984.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(II)	43154	4-phenylbutyl 4-methylbenzenesulfonate		C₁₇H₂₀O₃S	详情	详情
(IV)	43156	1-(benzyloxy)-4-bromobenzene; benzyl 4-bromophenyl ether	6793-92-6	C₁₃H₁₁BrO	详情	详情
(V)	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
(VI)	43157	1-benzyl-4-[4-(benzyloxy)phenyl]-4-piperidinol		C₂₅H₂₇NO₂	详情	详情
(VII)	43158	4-(1-benzyl-1,2,3,6-tetrahydro-4-pyridinyl)phenol		C₁₈H₁₉NO	详情	详情
(VIII)	43159	4-(4-piperidinyl)phenol		C₁₁H₁₅NO	详情	详情

Extended Information