Sodium Iodide → HCID 53725875, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-bromo,chloro-N-(2,6-dimethylphenyl)acetamide (V: 24.2 g, 0.10 mol), anhydrous sodium carbonate (15.9 g, 0.15 mol), sodium iodide (0.10 g) and 1-piperazine carboxaldehyde (IV: 10.3 mL, 0.10 mol) in anhydrous dimethylformamide (200 mL) was heated to 85° C. for 6 h before it was cooled, suction-filtered and concentrated down in vacuo. The residue was then dissolved in a minimal amount of hot 5% methanol in ethyl acetate. After 2 h at ambient temperature, the mixture was suction-filtered and the filtrate was concentrated down once again to yield a grey-colored solid which was recrystallized from ethyl acetate. There the Formula III compound was isolated 17.95 g (65%) as a white solid, m.p. 139°-140° C.; 1H NMR (300 MHz, CDCl3) δ 8.50 (br s, 1H), 7.99 (s, 1H), 7.25-7.03 (m, 3H), 3.59-5.56 (m, 2H), 3.42-3.39 (m, 2H), 3.17 (s, 2H), 2.66-2.59 (m, 4H), 2.19 (s, 6H); 13C NMR (75 MHz, CDCl3) ppm 167.96, 160.96, 135.18, 133.67, 128.53, 127.55, 61.89, 54.28, 53.21, 45.69, 40.07, 18.83; IR (KBr) 3432, 3274, 2958, 1672, 1506, 1446, 1436, 1148, 1020, 1008, 788 cm-1 ; MS m/z calc'd for C15H22N3O2 276.1712, found 276.1709.

Provenance & Evidence