2-Morpholinoethylamine → 2-Methyl-4-(n-2-morpholinoethyl)amino-8-(2,4,6-tri-methylphenyl)-quinoline

Participants

Reaction Conditions

Reaction Steps

Part C: To a solution of 5.1 g (17.1 mmol) of 2-methyl-4-chloro-8-(2,4,6-trimethylphenyl)-quinoline and 2.68 g (20.6 mmol) of 2-morpholinoethylamine in 150 ml of toluene, after bubbling through nitrogen gas for 30 minutes, a quantity of 2.29 g (23.9 mmol) sodium tertiary butoxide, 0.16 g (0.26 mmol) of 2,2′-bis(diphenylphosphino)-1,1′-binaphtyl (BINAP) and 0.082 g (0.09 mmol) Pd2(dibenzylideneacetone)3 were subsequently added. After heating to 100° C. for 16 hours and subsequent cooling, the reaction mixture was filtered and concentrated in vacuo. The product was purified on a silicagel column using CH2Cl2/MeOH/NH4OH 93:7:0.5 as the eluent. A total of 2.65 g of 2-methyl-4-(N-2-morpholinoethyl)amino-8-(2,4,6-tri-methylphenyl)-quinoline was obtained (40% yield).

Provenance & Evidence