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ChemicalBook CAS DataBase List VILAZODONE
163521-12-8

VILAZODONE synthesis

3synthesis methods
143612-79-7 Synthesis
3-(4-Chlorbutyl)-1H-indol-5-carbonitril

143612-79-7
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VILAZODONE

163521-12-8
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Yield:163521-12-8 95.7%

Reaction Conditions:

Stage #1:3-(4-chlorobutyl)-5-cyanoindole with sodium iodide in N,N-dimethyl-formamide at 25 - 30; for 0.25 h;
Stage #2:5-(1-piperazinyl)benzofuran-2-carboxamide with tetrabutylammomium bromide;sodium hydrogencarbonate in N,N-dimethyl-formamide at 110 - 115; for 1.25 h;Reagent/catalyst;Temperature;Time;Solvent;

Steps:

11.11e Preparation of Form I of vilazodone free base
To a solution of 3-(4-chlorobutyl)-1 H-indole-5-carbonitrile (2.5 g) in DMF (10 mL), sodium iodide (0.8 g) was added and the reaction mass was stirred at about 25-30 °C for 15 minutes. Sodium bicarbonate (3.61 g), 5-(piperazin-1 -yl)benzofuran-2- carboxamide (3 g) and tetrabutylammonium bromide (0.51 g) was added to the reaction mass and heated to 110-115 °C for 1 hour and 15 minutes. The reaction mass was then allowed to cool to 60 °C and water (37.5 mL) was added to the reaction mass slowly. The resulting precipitate was stirred for 60 minutes at about 30 °C. The precipitate was filtered, washed with water (10 mL) and dried for 5-6 hours at 60 °C under vacuum to afford the desired compound.Yield: 4.5 g (95.7 %). Purity (by HPLC): 97.39 %

References:

DR.REDDYS LABORATORIES LIMITED;IQBAL, Javed;ORUGANTI, Srinivas;RAPOLU, Rajesh Kumar;PEDDY, Vishweshwar;BOGE, Rajesham;PATHIVADA, Deepika;VELAGA, Dharma Jagannadha Rao;YARRAGUNTLA, Sesha Reddy;BADDAM, Sudhakar Reddy;NAREDLA, Anitha;DONIPARTHI, Kiran Kumar;NADGOUD, Ramesh Kumar;PAGADALA, Narasimha Rao;UNNIARAN, Syam Kumar;RAMAKRISHNAN, Srividya WO2013/168126, 2013, A1 Location in patent:Page/Page column 75-78

FullText

1422956-25-9 Synthesis
5-[4-[4-(5-cyano-1H-indol-3-yl)butyl]-1-piperazinyl]-2-benzofurancarboxylic acid ethyl ester hydrochlorid

1422956-25-9
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VILAZODONE

163521-12-8
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