Acetic Acid → Ammonium Hydroxide

Participants

Reaction Steps

To a solution of 4-[4-[[2-[2-(3,5-dimethylphenyl)-1H-indol-3-yl]ethyl]amino]butyl]phenol (19 mg in 1 mL methanol) was added 0.020 mL of a 37% solution of formaldehyde in water followed by 0.010 mL acetic acid and 16 mg of sodium cyanoborohydride and the mixture stirred at room temperature. After 26 hours the reaction was quenched by the addition of acetic acid, concentrated in vacuo and the excess acetic acid removed by toluene azeotrope. Purification of the concentrate by flash chromatography on silica gel (methylene chloride:methanol, 93.5:6.5; then methylene chloride:methanol:ammonium hydroxide, 90:10:1) gave the title compound (20 mg). m/e=427 (M+H)

Provenance & Evidence