5-chloro-1-(4-fluorophenyl)-3-(1,2,3,6-tetrahydro-4-pyridinyl)-1H-indole -Drug Synthesis Database

【结构式】

【分子编号】59587

【品名】5-chloro-1-(4-fluorophenyl)-3-(1,2,3,6-tetrahydro-4-pyridinyl)-1H-indole

【CA登记号】

【分子式】C₁₉H₁₆ClFN₂

【分子量】326.8006232

【元素组成】C 69.83% H 4.93% Cl 10.85% F 5.81% N 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：(X)

Acid-catalyzed condensation of 4-piperidone hydrate hydrochloride (IX) with indole (IV) produced the tetrahydropyridyl indole (X). This was alkylated with 1-(2-chloroethyl)imidazolinone (XII), (prepared by chlorination of the corresponding hydroxyethyl imidazolinone (XI)) to afford the N-substituted tetrahydropyridine (XIII). The target piperidine derivative was then obtained by catalytic hydrogenation of tetrahydropyridine (XIII).

参考文献中间体

合成目标

【1】 Perregaard, J.K. (H. Lundbeck A/S); Heterocyclic cpds.. AU 8655901; EP 0200322; ES 8707499; JP 1986236764; US 4710500 .
【2】 Perregaard, J.K.; Costall, B. (H. Lundbeck A/S); Piperidyl-substd. indoles. EP 0533824; JP 1993509080; US 5439922; WO 9200070 .
【3】 Bech Sommer, M. (H. Lundbeck A/S); Method of manufacturing sertindole. WO 9851685 .
【4】 Bogeso, K.P.; Hyttel, J.; Sanchez, C.; Arnt, J.; Perregaard, J.; Noncataleptogenic, centrally acting dopamine D-2 and serotonin 5-HT2 antagonists within a series of 3-substituted 1-(4-fluorophenyl)-1H-indoles. J Med Chem 1992, 35, 6, 1092.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(IV)	59582	5-chloro-1-(4-fluorophenyl)-1H-indole		C₁₄H₉ClFN	详情	详情
(IX)	18178	4,4-piperidinediol	73390-11-1	C₅H₁₁NO₂	详情	详情
(X)	59587	5-chloro-1-(4-fluorophenyl)-3-(1,2,3,6-tetrahydro-4-pyridinyl)-1H-indole		C₁₉H₁₆ClFN₂	详情	详情
(XI)	59588	1-(2-hydroxyethyl)-2-imidazolidinone	3699-54-5	C₅H₁₀N₂O₂	详情	详情
(XII)	21329	1-(2-chloroethyl)-2-imidazolidinone	2387-20-4	C₅H₉ClN₂O	详情	详情
(XIII)	59589	1-{2-[4-[5-chloro-1-(4-fluorophenyl)-1H-indol-3-yl]-3,6-dihydro-1(2H)-pyridinyl]ethyl}-2-imidazolidinone	106516-54-5	C₂₄H₂₄ClFN₄O	详情	详情

Extended Information