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【结 构 式】

【分子编号】49722

【品名】4-[3-[2-(dimethylamino)ethyl]-1H-indol-5-yl]-1-methyl-4-piperidinol

【CA登记号】

【 分 子 式 】C18H27N3O

【 分 子 量 】301.432

【元素组成】C 71.72% H 9.03% N 13.94% O 5.31%

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:(XI)

Condensation between 5-bromoindole (I) in ether and oxalyl chloride (II) in dichloromethane followed by treatment with dimethylamine provides N,N-dimethyaminoglyoxyl derivative (III), which is then reduced with LiAlH4 in THF to yield compound (IV). Coupling of (IV) with benzoyl chloride (V) by means of Et3N and DMAP in dichloromethane affords benzoylindole derivative (VI), which is then subjected to reaction with tributylstannyl derivative (VII) in toluene in the presence of Pd(PPh3)4 to furnish compound (VIII). Treatment of (VIII) with NaOH in refluxing MeOH gives indole (IX), which is converted into the final product by reduction with LiAlH4 in refluxing THF) and treatment with HCl for the formation of the corresponding hydrochloride salt. Alternatively, the target compound can be obtained as follows: treatment of (IV) with KH in ether and tert-butyllithium in pentane followed by reaction with N-methylpiperidinone (X) affords hydroxy derivative (XI), which is finally converted into the desired product.

1 Arora, J.; et al.; 5-Bicyclopiperidinetryptamine derivatives as selective 5-HT1D agonists. Soc Neurosci Abst 2000, 26, Part 1, Abst 145.14.
2 Slassi, A.; Edwards, L.; Meng, Q.; Rakhit, S. (NPS Allelix Corp.); 5-Cyclo indole cpds. as 5-HT1D receptor ligands. EP 0944595; JP 2001504501; WO 9823587 .
3 Rakhit, S.; Edwards, L.; Slassi, A.; Meng, Q. (NPS Allelix Corp.); 5-Cyclo indole cpds.. US 5998438 .
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) 13309 5-Bromo-1H-indole; 5-Bromoindole 10075-50-0 C8H6BrN 详情 详情
(II) 29841 Oxalyl chloride; 2-Chloro-2-oxoacetyl chloride 79-37-8 C2Cl2O2 详情 详情
(III) 40926 2-(5-bromo-1H-indol-3-yl)-N,N-dimethyl-2-oxoacetamide C12H11BrN2O2 详情 详情
(IV) 49717 N-[2-(5-bromo-1H-indol-3-yl)ethyl]-N,N-dimethylamine; 2-(5-bromo-1H-indol-3-yl)-N,N-dimethyl-1-ethanamine C12H15BrN2 详情 详情
(V) 10463 Benzoyl chloride 98-88-4 C7H5ClO 详情 详情
(VI) 49718 [5-bromo-3-[2-(dimethylamino)ethyl]-1H-indol-1-yl](phenyl)methanone C19H19BrN2O 详情 详情
(VII) 49719 tert-butyl 4-(tributylstannyl)-3,6-dihydro-1(2H)-pyridinecarboxylate C22H43NO2Sn 详情 详情
(VIII) 49720 tert-butyl 4-[1-benzoyl-3-[2-(dimethylamino)ethyl]-1H-indol-5-yl]-3,6-dihydro-1(2H)-pyridinecarboxylate C29H35N3O3 详情 详情
(IX) 49721 tert-butyl 4-[3-[2-(dimethylamino)ethyl]-1H-indol-5-yl]-3,6-dihydro-1(2H)-pyridinecarboxylate C22H31N3O2 详情 详情
(X) 10919 1-Methyl-4-piperidone; 1-Methyltetrahydro-4(1H)-pyridinone; N-Methyl-4-piperidone;1-methylpiperidin-4-one 1445-73-4 C6H11NO 详情 详情
(XI) 49722 4-[3-[2-(dimethylamino)ethyl]-1H-indol-5-yl]-1-methyl-4-piperidinol C18H27N3O 详情 详情
Extended Information