Synthesis
GENERAL STEPS: 4-Cyanobenzyl bromide (10 g, 0.05 mol), sodium carbonate (5.95 g, 56.0 mmol, 1.1 eq.) and dimethylamine (56.0 mmol, 1.1 eq.) were dissolved in N,N-dimethylformamide (75 mL) and stirred at room temperature for 3 hours. The reaction mixture was then heated to 90°C to continue the reaction. After completion of the reaction, it was cooled to room temperature, water (200 mL) was added and stirred at 0°C. The reaction was carried out at 0°C with the addition of water. If crystals precipitated, they were collected by filtration, washed with cold water (2 x 50 mL) and dried under vacuum to give the first products. The filtrates were combined and extracted with ethyl acetate (3 x 50 mL), the organic phase was dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the second product. The total yield of the products was 72-98%.
References
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[4] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 17, p. 5891 - 5908
[5] Archiv der Pharmazie, 1962, vol. 295 /67, p. 690 - 697