Sulfuric acid magnesium salt (1:1) → N-(quinolin-8-ylmethyl)cyclopropanamine

Participants

Reaction Steps

To a dichloromethane (0.13 M) solution of 8-quinolinecarbaldehyde (1 eq.) was added magnesium sulphate (1 eq.) and cyclopropyl amine (2 eq.). The resulting suspension was stirred at RT for 16 h. The insolubles were removed via filtration and rinsed with dichloromethane before the combined filtrate was concentrated in vacuo. The crude imine thus obtained was taken up in methanol (0.13 M) and then added sodium borohydride (1.5 eq.) portionwise. The reaction mixture was stirred at RT for 2 h before it was quenched with 1 N aq. HCl. The pH of the solution was then adjusted to ˜10 with 1 N aq. NaOH before it was extracted with ether. The combined organic extracts were washed further with water and brine, dried over Na2SO4, filtered and the filtrate concentrated in vacuo to afford the crude title compound as a yellow oil.

Provenance & Evidence