Acetic Acid → 7-(3-Chlorobenzylamino)-1,2,3,3a,7,8,9,10b-octahydro-dicyclopenta[c,g]quinolin-4-one

Participants

Reaction Steps

A solution of 400 mg (1.66 mmol) of 1,2,3,3a,7,8,9,10b-octahydro-dicyclo-penta[c,g]quinoline-4,7-dione in 50 ml of 1,2-dichloroethane and 50 ml of THF is mixed with 0.22 ml (1.82 mmol) of 3-chlorobenzylamine, 526 mg (2.49 mmol) of sodium (triacetoxy)borohydride and 0.01 ml (0.17 mmol) of acetic acid. After 24 hours at room temperature, 0.44 ml (3.6 mmol) of 3-chlorobenzylamine, 1.05 g (5.0 mmol) of sodium(triacetoxy)-borohydride and 0.02 ml (0.34 mmol) of acetic acid are added to it and stirred for another 24 hours at room temperature. The reaction solution is diluted with ethyl acetate, washed with water, dried (Na2SO4) and concentrated by evaporation in a vacuum. Column chromatography on silica gel with hexane-ethyl acetate yields 360 mg of 7-(3-chlorobenzylamino)-1,2,3,3a,7,8,9,10b-octahydro-dicyclopenta[c,g]quinolin-4-one.

Provenance & Evidence