2,3-Dihydro-1,4-benzodioxin-6-methylamine → 1-(2-(4-((2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)cyclohexyl)ethyl)-7-methoxy-4-methylquinolin-2(1H)-one

Participants

Reaction Steps

To 2 mL of methanol solution containing 45 mg of 7-methoxy-4-methyl-1-(2-(4-oxocyclohexyl)ethyl)quinolin-2(1H)-one and 21 mg of (2,3-dihydrobenzo[b][1,4-]dioxin-6-yl)methylamine, 10 μL of acetic acid and 12 mg of sodium cyanoborohydride were added, and stirred at the same temperature for 30 min. To the reaction mixture, water, chloroform and aqueous saturated sodium hydrogen carbonate solution were added. The organic layer was separated, washed with aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by flash silica gel column chromatography [eluent; chloroform:methanol=20:1], to give (A) 5.4 mg of 1-(2-(4-((2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)cyclohexyl)ethyl)-7-methoxy-4-methylquinolin-2(1H)-one as a yellow oil and (B) 17 mg of 1-(2-(4-((2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)cyclohexyl)ethyl)-7-methoxy-4-methylquinolin-2(1H)-one as a pale yellow foam.

Provenance & Evidence