Sodium Carbonate → 1-(3-Aminophenyl)2-[4-(2-methyl-5-quinolinyl)-1-piperazinyl]ethanol

Participants

Reaction Steps

Sodium carbonate (1.5 eq) and 2-bromo-1-(3-nitrophenyl)ethanone (1.5 eq) were added to a stirred solution of 2-methyl-5-(1-piperazinyl)quinoline (D3) (1 eq) in tetrahydrofuran at room temperature under an inert atmosphere, and the reaction was left under stirring for 1 h. The solution was then diluted with MeOH, NaBH4 (2 eq) was added and the reaction was left under stirring for 1 h. The solvent was removed under reduced pressure. The crude material was purified on SPE cartridge (SCX) using as eluant a gradient from MeOH to MeOH:CH2Cl2 (1:1) and then 2M NH3 in MeOH affording an intermediate which was reduced following a similar procedure to D6 to give the title compound in 55% yield.

Provenance & Evidence