Potassium Carbonate → (+/-) trans-4,5,5a,6,7,8,9,9a-Octahydro-6-propyloxazolo[4,5-f]quinolin-2-amine

Participants

Reaction Steps

A mixture of (±) trans-4,5,5a,6,7,8,9,9a-octahydrooxazolo[4,5-f]quinolin-2-amine, 1.46 g (5.0 mmol), 3.6 g (26 mmol) of finely ground potassium carbonate and 2.5 ml (25.6 mmol) of 1-iodopropane in 250 ml of acetonitrile is refluxed, under nitrogen, for 24 hours. The mixture is cooled, filtered through a pad of Celite, concentrated and partitioned between brine and chloroform. The organic extract is dried and concentrated. Chromatography of the mixture on silica gel gives (±) trans-4,5,5a,6,7,8,9,9a-octahydro-6-propyloxazolo[4,5-f]quinolin-2-amine. The procedure just described can be applied to (±) trans-4,5,5a,6,7,8,9,9a-octahydrooxazolo[5,4-f]quinolin-2-amine to give (±) trans-4,5,5a,6,7,8,9,9a-octahydro-6-propyloxazolo [5,4-f]quinolin-2-amine.

Provenance & Evidence