A mixture of 10.0 grams of β-dimethylaminoethanol and 1.9 grams of sodium
in 90 cc of dry xylene was heated at 95°C for 5 hours. To the resulting
solution was added at 30°C, 18 grams of 3-butyl-1-chloroisoquinoline. The
solution, which turned very dark, was heated at 100°-125°C for 3.5 hours.
The mixture was extracted with two 100 cc portions of 2N hydrochloric acid
solution. The acid solution was made strongly alkaline with 40% potassium
hydroxide solution and the oil which separated was taken into ether. The ether
solution was washed with two 100 cc portions of water saturated with sodium
chloride, and then dried over anhydrous sodium sulfate for 3 hours. The
sodium sulfate was removed by filtration and the ether by distillation.
Distillation of the residual oil gave a colorless liquid, BP 155°-157°C/3mm.
