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Chapter – 5 Synthesis and Characterization…..
4-[(2-CHLORO PHENYL) AMINO]-3-[(4-ETHYL PIPERAZIN-1-YL)
METHYL]-2H-CHROMEN-2-ONE (DNJ-1004): IR (KBr, cm -1 ): 3389 (-NH),
3070 (Ar-H, str), 2966 (-CH3), 2810 (-CH2), 1707 (>CO), 1570, 1490, 1470,
1440 (Ar-H, ben), 1336 (C-N, Ar, 3°), 1305 (C-N, Ar, 2°), 1060 (C-O-C), 871
(C-Cl), 755 (1,2-di sub); MS m/z = 397 (M + ); Anal. Calcd. for C22H24ClN3O2: C,
66.41; H, 6.08; N, 10.56. Found: C, 66.39; H, 6.05; N, 10.53.
4-[(3-CHLORO PHENYL) AMINO]-3-[(4-ETHYL PIPERAZIN-1-YL)
METHYL]-2H-CHROMEN-2-ONE (DNJ-1005): IR (KBr, cm -1 ): 3390 (-NH),
3071 (Ar-H, str), 2967 (-CH3), 2810 (-CH2), 1706 (>CO), 1572, 1488, 1475,
1440 (Ar-H, ben), 1338 (C-N, Ar, 3°), 1306 (C-N, Ar, 2°), 1076 (C-O-C), 865
(C-Cl), 770 (1,3-di sub); 1 H NMR (300 MHz, CDCl3): δ (ppm) 1.13 (3H, s),
2.50 (4H, m), 2.62 (6H, s), 3.76 (2H, s), 6.78 (1H, dd, J = 1.635 Hz, J = 1.428
Hz), 6.92 (1H, t), 7.05 (2H, m, J = 0.957 Hz), 7.21 (1H, s), 7.34 (2H, m, J =
1.233 Hz, J = 0.723 Hz), 7.48 (1H, dd, J = 1.389 Hz, J = 1.149 Hz, J = 1.362
Hz), 10.41 (1H, s); 13 C NMR (300 MHz, CDCl3): δ (ppm) 162.89, 154.05,
151.98, 143.99, 135.41, 131.84, 130.67, 126.30, 123.46, 123.31, 120.77,
118.97, 117.80, 115.53, 105.13, 54.76, 53.43, 52.70, 52.65, 12.43; MS m/z =
397 (M + ); Anal. Calcd. for C22H24ClN3O2: C, 66.41; H, 6.08; N, 10.56. Found:
C, 66.44; H, 6.09; N, 10.55.
4-[(4-CHLORO PHENYL) AMINO]-3-[(4-ETHYL PIPERAZIN-1-YL)
METHYL]-2H-CHROMEN-2-ONE (DNJ-1006): IR (KBr, cm -1 ): 3370 (-NH),
3080 (Ar-H, str), 2967 (-CH3), 2810 (-CH2), 1706 (>CO), 1572, 1488, 1475,
1440 (Ar-H, ben), 1337 (C-N, Ar, 3°), 1307 (C-N, Ar, 2°), 1050 (C-O-C), 869
(C-Cl), 812 (1,4-di sub); MS m/z = 397 (M + ); Anal. Calcd. for C22H24ClN3O2: C,
66.41; H, 6.08; N, 10.56. Found: C, 66.40; H, 6.07; N, 10.58.
3-[(4-ETHYL PIPERAZIN-1-YL) METHYL]-4-[(2-FLUORO PHENYL)
AMINO]-2H-CHROMEN-2-ONE (DNJ-1007): IR (KBr, cm -1 ): 3381 (-NH),
3070 (Ar-H, str), 2962 (-CH3), 2811 (-CH2), 1707 (>CO), 1570, 1484, 1470,
1438 (Ar-H, ben), 1337 (C-N, Ar, 3°), 1306 (C-N, Ar, 2°), 1054 (C-O-C), 990
(C-F), 750 (1,2-di sub); MS m/z = 381 (M + ); Anal. Calcd. for C22H24FN3O2: C,
69.27; H, 6.34; N, 11.02. Found: C, 69.23; H, 6.38; N, 11.05.
Department of Chemistry, Saurashtra University, Rajkot – 360 005 309