HCID 20150321, compound → HCID 20150294, compound

Participants

Reaction Steps

4-{[2-(4-Nitrophenyl)-4-quinolyl]oxyacetyl}morpholine (3.93 g), prepared according to Example 31, dissolved in methanol (80 cc) is hydrogenated at 40° C. for 30 minutes and then at room temperature (approximately 20° C.) and under atmospheric pressure in the presence of a 5N solution (4 cc) of hydrochloric acid in isopropanol and palladinized charcoal (10% Pd) (0.4 g) as catalyst. After absorption of the theoretical amount of hydrogen, normal sodium hydroxide solution (25 cc) is added to the reaction mixture in order to redissolve the precipitate formed. After filtration, the solvent is removed under reduced pressure and the residual aqueous phase is taken up with methylene chloride. The organic phase is washed with water, dried over magnesium sulphate and evaporated under reduced pressure. The residue (2.9 g) is dissolved in hot ethyl acetate (15 cc); ethyl ether (30 cc) is then added, and the precipitate is filtered off and chromatographed on silica gel using a toluene/methanol/diethylamine (90:5:5 by volume) mixture. 4-{[2-(4-Aminophenyl)-4-quinolyl]oxyacetyl}morpholine (1.05 g), m.p. 174° C., is thereby isolated.

Provenance & Evidence