Potassium Carbonate → HCID 19350310, compound

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Reaction Steps

Under an Ar atmosphere, 2.16 ml p-fluorobenzaldehyde and 3 ml DMSO were added sequentially to 3.5 g (30 mmol) of anhydrous K2CO3, 3.70 ml (20 mmol) diallylamine. With constant stirring, the mixture was heated to about 155°-160° C. After refluxing for 20 hours, the solution became intense red. The mixture was cooled to room temperature and 10 ml distilled water was added to dissolve any inorganic salts and the product was extracted with ether. The water layer was washed with ether several times and the combined organic layers were dried over MgSO4. The ether solution was then filtered and the ether, unreacted starting materials and solvent DMSO were removed by vacuum distillation at 100° C. A very viscous orange red product was left in the flask. Yield=2.05 g (51%). Mass spectrum: M+ /e=201. Calcd. M+ /e=201.27 Anal. calcd. for C13H15NO, C, 77.58; H, 7.51; N, 6.96. Found: C, 77.33; H, 7.33; N, 6.66. 1H NMR(CDCl3), δ 9.71 (1H,s), 7.70 (2H, d, J=9Hz), 6.70 (2H, d, J=9Hz), 5.82 (2H, m), 5.19 (4H, m), 4.00 (4H,t). 13C NMR (CDCl3) δ 189.4, 152.8, 131.8, 116.8, 110.9, 52.22 ppm.

Provenance & Evidence