Reacción #515739

Ecuación de reacción

acetic acid

4-(5-methoxy-1H-indol-3-yl)-cyclohexanone

1-(indol-4-yl)piperazine

sodium triacetoxyborohydride

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product

Rendimiento 55.1%

5-Methoxy-3-[cis-4-[4-(1H-indol-4-yl)-1-piperazinyl]cyclohexyl]-1H-indole

Rendimiento 55.1%

Disolventes

1,2-dichloroethane

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe reaction was quenched with 1N sodium hydroxide (10 ml)
2. 2
   Extracciónextracted with methylene chloride (3×60 ml)
3. 3
   Lavadowashed with brine (3×60 ml)
4. 4
   SecadoThe organic layer was dried over anhydrous sodium sulfate
5. 5
   Filtraciónfiltered

Procedimiento

A solution of 4-(5-methoxy-1H-indol-3-yl)-cyclohexanone (1.2 g, 5 mmol), 1-(indol-4-yl)piperazine (1 g, 5 mmol), sodium triacetoxyborohydride (1.47 g, 6.2 mmol) and acetic acid (0.28 ml, 4 mmol) in 1,2-dichloroethane (20 ml) was allowed to stir at room temperature overnight. The reaction was quenched with 1N sodium hydroxide (10 ml), extracted with methylene chloride (3×60 ml) and washed with brine (3×60 ml). The organic layer was dried over anhydrous sodium sulfate and filtered. Chromatography (2.5% methanol-ethyl acetate) afforded 1.18 g (55%) of product as a white solid: mp 105-108° C.

Fuente