Sulfuric acid magnesium salt (1:1) → {2-[2-(3,5-Dimethyl-phenyl)-1H-indol-3-yl]-ethyl}-(5-pyridin-4-yl-pentyl)-amine

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-[2-(3,5-dimethylphenyl)-1H-indol-3-yl]-ethylamine (162 mg) and 5-(4-pyridyl)-pentanal (100 mg in 2 mL dry chloroform) was added anhydrous magnesium sulfate (735 mg) and the mixture stirred at 0° C. for 15 minutes. At this time sodium borohydride (92.7 mg) was added followed by 3 mL dry methanol and the mixture stirred at 0° C. After 1 hour, the reaction was quenched by pouring into water (25 mL), stirred for 30 minutes then extracted with methylene chloride (4×25 mL). The combined organics were dried over potassium carbonate, concentrated in vacuo and the residue purified by flash chromatography on silica gel (methylene chloride:methanol, 95:5) to give the title compound (172 mg). m/e=412 (M+H)

Provenance & Evidence