4-(2-di-N-propylaminoethyl)indole synthesis
- Product Name:4-(2-di-N-propylaminoethyl)indole
- CAS Number:76149-15-0
- Molecular formula:C16H24N2
- Molecular Weight:244.38
Yield:76149-15-0 85%
Reaction Conditions:
Stage #1: 2-(1H-indol-4-yl)ethan-1-amine;propionic acidwith sodium tetrahydroborate at 55 - 60; for 20 h;
Stage #2: with sodium hydroxide in water at 20;
Steps:
3.A
NaBH4 (4.8g, 126. 9mmol) was added to a mixture of 4-[(2-amino) ethyl] indole (III) (4g, 24. 9mmol) and propionic acid (27.8mL, 374. 4mmol) under inert atmosphere previously heated at 60°C and the reaction mixture was stirred at 55-60°C for 20 hours. When the reaction mixture reached room temperature, NaOH 2N (80mL) was added and was then washed with toluene. The organic layer was washed with NaOH 2N to obtain, 5.2g (85%) of 4- [2- (dipropylamino) ethyl] indole (IV). 1H-RMN (200MHz, CDCI3) δ: 0,91 (t, J =7,3Hz, 6H, CH3), 1,55 (m, 4H, CH2-CH3), 2,53 (m, 4H, NCH2-CH2-CH3), 3.0 (m, 4H, Ar-CH2-CH2-N), 6,58 (m, 1H, 3-H), 6,90-7, 40 (m, 4H, Ar), 8,50 (broad, 1H,-NH).
References:
WO2005/40115,2005,A1 Location in patent:Page/Page column 5
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