Reacción #515740

Ecuación de reacción

acetic acid

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

1-(indol-4-yl)piperazine

sodium triacetoxyborohydride

→

white solid

Rendimiento 40.7%

3-[cis-4-[4-(1H-Indol-4-yl)-1-piperazinyl]cyclohexyl]-2-methyl-1H-indole

Rendimiento 40.7%

Disolventes

1,2-dichloroethane

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe reaction was quenched with 1N sodium hydroxide (80 ml)
2. 2
   Extracciónextracted with methylene chloride (3×300 ml)
3. 3
   Lavadowashed with brine (150 ml)
4. 4
   SecadoThe organic layer was dried over anhydrous sodium sulfate
5. 5
   Filtraciónfiltered
6. 6
   OtroThe solvent was removed under vacuum
7. 7
   Otroto afford an off-white solid
8. 8
   FiltraciónTrituration of the solid with warm methylene chloride (80 ml) followed by filtration

Procedimiento

A solution of 4-(1H-indol-3-yl)-cyclohexanone (1.44 g, 6.33 mmol), 1-(indol-4-yl)piperazine (1.27 g, 6.33 mmol), sodium triacetoxyborohydride (1.88 g, 8.86 mmol) and acetic acid (0.76 mg, 12.6 mmol) in 1,2-dichloroethane (100 ml) was allowed to stir at room temperature overnight. The reaction was quenched with 1N sodium hydroxide (80 ml), extracted with methylene chloride (3×300 ml), and washed with brine (150 ml). The organic layer was dried over anhydrous sodium sulfate and filtered. The solvent was removed under vacuum to afford an off-white solid. Trituration of the solid with warm methylene chloride (80 ml) followed by filtration afforded 0.88 g of white solid. The mother liquor was concentrated and chromatographed (2% methanol-methylene chloride) to afford another 0.18 g (total yield 40.7%) of product as a white solid: mp 279-280° C.

Fuente