[4-[2-(1-piperidinyl)ethoxy]phenyl]methanol -Drug Synthesis Database

【结构式】

【分子编号】35796

【品名】[4-[2-(1-piperidinyl)ethoxy]phenyl]methanol

【CA登记号】

【分子式】C₁₄H₂₁NO₂

【分子量】235.32628

【元素组成】C 71.46% H 8.99% N 5.95% O 13.6%

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：(IV)

Alkylation of p-hydroxybenzaldehyde (I) with 1-(2-chloroethyl)piperidine (II) afforded 4-(2-piperidinylethoxy)benzaldehyde (III). Aldehyde function reduction using NaBH4 provided the benzylic alcohol (IV). Alternatively, alcohol (IV) can be obtained by reaction of 4-hydroxybenzyl alcohol (A) with 1-(2-chloroethyl)piperidine hydrochloride (II) by means of NaOH and benzyl triethylammonium bromide in toluene.The hydrochloride salt of (IV) was then treated with SOCl2 to furnish chloride (V).

参考文献中间体

合成目标

【1】 Silvestre, J.S.; Sorbera, L.A.; Castaner, J.; Pipendoxifene. Drugs Fut 2002, 27, 10, 942.
【2】 Vid, G.; Potoski, J.R.; Raveendranath, P.; Zeldis, J.; Ren, J. (American Home Products Corp.); Novel aryloxy-alkyl-dialkylamines. EP 1025077; WO 9919293 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(A)	29474	4-(hydroxymethyl)phenol; 4-hydroxyphenylmethanol 4-hydroxybenzenemethanol; 4-Hydroxybenzyl alcohol	623-05-2	C₇H₈O₂	详情	详情
(I)	13433	4-Hydroxybenzaldehyde; p-Hydroxybenzaldehyde	123-08-0	C₇H₆O₂	详情	详情
(II)	10117	1-(2-Chloroethyl)piperidine; N-(2-Chloroethyl)piperidine	1932-03-2	C₇H₁₄ClN	详情	详情
(III)	35795	4-[2-(1-piperidinyl)ethoxy]benzaldehyde	26815-04-3	C₁₄H₁₉NO₂	详情	详情
(IV)	35796	[4-[2-(1-piperidinyl)ethoxy]phenyl]methanol		C₁₄H₂₁NO₂	详情	详情
(V)	46522	1-[2-[4-(chloromethyl)phenoxy]ethyl]piperidine; 4-(chloromethyl)phenyl 2-(1-piperidinyl)ethyl ether		C₁₄H₂₀ClNO	详情	详情

合成路线2

该中间体在本合成路线中的序号：(IV)

Alkylation of 4-hydroxybenzaldehyde (I) with 1-(2-chloroethyl)piperidine hydrochloride (II) in the presence of K2CO3 yielded (piperidinylethoxy)benzaldehyde (III), which was further reduced to the benzylic alcohol (IV) with methanolic NaBH4. Coupling of (IV) with thioacetic acid according to the Mitsunobu procedure yielded thioacetate ester (V), which was converted to the corresponding thiol (VI) by reductive cleavage of the thioester group with LiAlH4.

参考文献中间体

合成目标

【1】 Leblanc, G.; Noël, P.; Poirier, D.; Labrie, F.; Breton, E.; Luu-The, V.; Tremblay, M.R.; Spironolactone-related inhibitors of type II 17beta-hydroxysteroid dehydrogenase: Chemical synthesis, receptor binding affinities, and proliferative/antiproliferative activities. Bioorg Med Chem 1999, 7, 6, 1013.

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)	13433	4-Hydroxybenzaldehyde; p-Hydroxybenzaldehyde	123-08-0	C₇H₆O₂	详情	详情
(II)	10117	1-(2-Chloroethyl)piperidine; N-(2-Chloroethyl)piperidine	1932-03-2	C₇H₁₄ClN	详情	详情
(III)	35795	4-[2-(1-piperidinyl)ethoxy]benzaldehyde	26815-04-3	C₁₄H₁₉NO₂	详情	详情
(IV)	35796	[4-[2-(1-piperidinyl)ethoxy]phenyl]methanol		C₁₄H₂₁NO₂	详情	详情
(V)	35797	S-[4-[2-(1-piperidinyl)ethoxy]benzyl] ethanethioate		C₁₆H₂₃NO₂S	详情	详情
(VI)	35798	4-[2-(1-piperidinyl)ethoxy]benzylhydrosulfide; [4-[2-(1-piperidinyl)ethoxy]phenyl]methanethiol		C₁₄H₂₁NOS	详情	详情

Extended Information