4-phenyl-1-butanamine; 4-phenylbutylamine -Drug Synthesis Database

【结构式】

【分子编号】37811

【品名】4-phenyl-1-butanamine; 4-phenylbutylamine

【CA登记号】13214-66-9

【分子式】C₁₀H₁₅N

【分子量】149.23584

【元素组成】C 80.48% H 10.13% N 9.39%

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：(III)

The title compound was prepared by treatment of 4-hydroxycinnamic acid (I) with CDI to produce the corresponding imidazolide (II), which was then coupled with 4-phenylbutyl amine (III) in THF at r.t.

参考文献中间体

合成目标

【1】 Yuen, P.-W.; Woodward, R.M.; Cai, S. X.; Schelkun, R.M.; Whittemore, E.R.; Keana, J.F.W.; Zhou, Z.-L.; Tamiz, A.P.; Weber, E.; Structure-activity relationship of N-(phenylalkyl)cinnamides as novel NR2B subtype-selective NMDA receptor antagonists. J Med Chem 1999, 42, 17, 3412.
【2】 Cai, S.X.; Keana, J.F.W.; Lan, N.C.; Araldi, G.L.; Tamiz, A.; Zhou, Z.-L.; Woodward, R.M.; Whittemore, E.R.; Weber, E. (Acea Pharmaceuticals; CoCensys, Inc.; Oregon Health Sciences University; University of Oregon); Subtype-selective NMDA receptor ligands and the use thereof. WO 9723202 .

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)	37809	(E)-3-(4-Hydroxyphenyl)-2-propenoic acid; 4-Hydroxy cinnamic acid	501-98-4	C₉H₈O₃	详情	详情
(II)	37810	(E)-3-(4-hydroxyphenyl)-1-(1H-imidazol-1-yl)-2-propen-1-one		C₁₂H₁₀N₂O₂	详情	详情
(III)	37811	4-phenyl-1-butanamine; 4-phenylbutylamine	13214-66-9	C₁₀H₁₅N	详情	详情

合成路线2

该中间体在本合成路线中的序号：(V)

The Friedel-Crafts' condensation of propionyl chloride (I) with 2,3-dihydrobenzo[b]thiophene (II) in dichloroethylene gives 5-propionyl-2,3-dihydrobenzo[b]thiophene (III), which is brominated with Br2 in THF yielding 5-(2-bromopropionyl)-2,3-dihydrobenzo[b]thiophene (IV). Finally this compound is condensed with 4-phenylbutylamine (V) in refluxing methanol and reduced with NaBH4 in the solvent

参考文献中间体

合成目标

【1】 Serradell, M.N.; Castaner, J.; Thorpe, P.J.; Tibalosin. Drugs Fut 1984, 9, 12, 909.
【2】 Lambellin, G.; Roba, J.; Gillet, C.; Roncocci, R. (Continental Pharma); BE 848496; FR 2370470; FR 2370472; GB 1565080; JP 7797952 .

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)	61080	2,3-dihydro-1-benzothiophene		C₈H₈S	详情	详情
(II)	15967	propanoyl chloride; propionyl chloride	79-03-8	C₃H₅ClO	详情	详情
(III)	61081	1-(2,3-dihydro-1-benzothiophen-6-yl)-1-propanone		C₁₁H₁₂OS	详情	详情
(IV)	61082	2-bromo-1-(2,3-dihydro-1-benzothiophen-6-yl)-1-propanone		C₁₁H₁₁BrOS	详情	详情
(V)	37811	4-phenyl-1-butanamine; 4-phenylbutylamine	13214-66-9	C₁₀H₁₅N	详情	详情

Extended Information