Acetic Acid → HCID 178433616, compound

Participants

Reaction Steps

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.

Provenance & Evidence