Reaktion #515742

Reaktionsgleichung

acetic acid

4-(5-cyano-1-n-propyl-indol-3-yl)-cyclohexanone

1-(indol-4-yl)piperazine

sodium triacetoxyborohydride

→

product

Ausbeute 15.0%

3-{(1,4-cis)-4-[4-(1H-indol-4-yl)-piperazin-1-yl]-cyclohexyl}-1-propyl-1H-indole-5-carbonitrile

Ausbeute 15.0%

Lösungsmittel

1,2-dichloroethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction was quenched with 1N sodium hydroxide (20 ml)
2. 2
   Extraktionextracted with methylene chloride (3×100 ml)
3. 3
   Waschenwashed with brine (3×100 ml)
4. 4
   TrocknenThe organic layer was dried over anhydrous sodium sulfate
5. 5
   Filtrationfiltered

Vorschrift

A solution of 4-(5-cyano-1-n-propyl-indol-3-yl)-cyclohexanone (1.68 g, 6 mmol), 1-(indol-4-yl)piperazine (1.27 g, 6.3 mmol), sodium triacetoxyborohydride (1.84 g, 8.9 mmol) and acetic acid (0.94 ml, 16 mmol) in 1,2-dichloroethane (80 ml) was allowed to stir at room temperature overnight. The reaction was quenched with 1N sodium hydroxide (20 ml), extracted with methylene chloride (3×100 ml) and washed with brine (3×100 ml). The organic layer was dried over anhydrous sodium sulfate and filtered. Chromatography (10% methanol-ethyl acetate) afforded 0.42 g(15%) of product as a white powder.

Quelle