HCID 19778092, compound → HCID 9796680, compound

Participants

Reaction Steps

(RS)-2-(1-azabicyclo[2.2.2]oct-3-yl)-1,2-dihydro-5-methyl-1-oxopyrido[4,3-b]indole hydrochloride (0.3 g, 0.98 mmol), from Example 3, in acetic acid (5 ml, containing 3 drops of 70% perchloric acid) was reduced with 20% palladium hydroxide on carbon (0.1 g) at 80° C. and 350 kPa for 20 hours. The catalyst was removed by filtration and the filtrate was concentrated under reduced pressure. The residue was dissolved in water (10 ml), basified with ammonium hydroxide solution and extracted with ethyl acetate. The ethyl acetate was dried over anhydrous potassium carbonate, filtered and evaporated. The residue was purified by column chromatography (10% methanol in dichloromethane +1% ammonium hydroxide; silica; Rf. 0.3) to afford 0.5 g (16% yield) of (RS)-2-(1-azabicyclo[2.2.2]oct-3-yl)-1,2,3,4-tetrahydro-5-methyl-1-oxopyrido[4,3-b]indole.

Provenance & Evidence