Indole → 3-(8-Aza-bicyclo[3.2.1]oct-2-en-3-yl)-1H-indole

Participants

Reaction Conditions

Reaction Steps

The reaction is performed by first dissolving the indole in a suitable solvent, typically acetic acid, and then adding a suitable acid, such as hydrochloric or phosphoric acid. The 3-tropanone is then added and the reaction heated at about 60-65° C. for from about 4 to about 24 hours. The resulting 3-(indol-3-yl)-8-azabicyclo-[3.2.1]oct-2-ene is isolated by pouring the reaction mixture into an ice water slurry, adjusting the pH of the aqueous mixture to about 8 by the addition of base, typically sodium hydroxide, and extracting with a water immiscible solvent, typically dichloromethane or ethyl acetate. The product recovered may be purified by crystallization or chromato-graphy as necessary or desired.

Provenance & Evidence