Sodium Hydroxide → HCID 70473200, compound

Participants

Reaction Conditions

Reaction Steps

558 g of sodium cyanoborohydride are added in portions to a suspension of 960 mg of 4-(2-chlorophenyl)-1H-indole in 11 ml of trifluoroacetic acid cooled to 0° C. The reaction medium is stirred for 16 hours while allowing it to rise to ambient temperature and then the pH is brought to neutrality with a sodium hydroxide solution. The reaction mixture is diluted with 300 ml of water then extracted with ethyl acetate (2×250 ml). The organic phases are combined and then concentrated to dryness under reduced pressure. After purification of the residue by silica column chromatography, elution being carried out with a mixture of heptane and ethyl acetate (80/20), 395 mg of 4-(2-chlorophenyl)-2,3-dihydro-1H-indole are obtained in the form of a colorless viscous oil.

Provenance & Evidence