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Chapter – 1 Preparation and Yield optimization.....
146.78, 129.90, 129.79, 129.75, 129.71, 129.64, 129.44, 127.56, 127.44,
127.40, 127.20, 126.71, 124.73, 124.68, 124.56, 124.05, 118.79, 118.35,
117.99, 116.36, 116.26, 115.69, 114.82, 114.78, 114.74, 114.32, 114.28,
109.66, 109.62, 109.49, 109.45, 108.94, 107.43, 107.24, 106.97, 106.77,
60.50, 56.66, 37.51, 14.19; MS m/z = 306 (M + ); Anal. Calcd. for C17H17F3N2:
C, 66.66; H, 5.59; N, 9.15. Found: C, 66.70; H, 5.54; N, 9.19.
3-METHYL-N-[(2-METHYL-2, 3-DIHYDRO-1H-INDOL-1-YL) METHYL]
ANILINE (DNJ-204): IR (KBr, cm -1 ): 3341 (-NH), 3056 (Ar-H), 2956 (–CH3),
2860 (–CH2), 1558, 1501, 1471, 1462 (Ar-H), 1386 (C-N, Ar, 3°), 1330 (C-N,
Ar, 2°), 846 (1,3-di sub.); MS m/z = 252 (M + ); Anal. Calcd. for C17H20N2: C,
80.91; H, 7.99; N, 11.10. Found: C, 80.95; H, 7.97; N, 11.08.
3-METHOXY-N-[(2-METHYL-2, 3-DIHYDRO-1H-INDOL-1-YL) METHYL]
ANILINE (DNJ-205): IR (KBr, cm -1 ): 3273 (-NH), 3051 (Ar-H), 2964 (–CH3),
2864 (–CH2), 1562, 1500, 1470, 1460 (Ar-H), 1380 (C-N, Ar, 3°), 1337 (C-N,
Ar, 2°), 1066 (C-O-C ), 885 (1,3-di sub.); MS m/z = 268 (M + ); Anal. Calcd. for
C17H20N2O: C, 76.09; H, 7.51; N, 10.44. Found: C, 76.05; H, 7.53; N, 10.48.
N-METHYL-N-[(2-METHYL-2, 3-DIHYDRO-1H-INDOL-1-YL) METHYL]
ANILINE (DNJ-206): IR (KBr, cm -1 ): 3025 (Ar-H), 2953 (–CH3), 2870 (–CH2),
1600, 1562, 1486, 1452 (Ar-H), 1362 (C-N, Ar, 3°); 1 H NMR (400 MHz,
CDCl3): δ (ppm) 1.32 (3H, m), 2.59 (2H, qt), 2.85 (3H, s), 4.43 (1H, q), 4.76
(2H, t), 6.68 (2H, m), 6.93 (2H, m), 7.05 (2H, m), 7.25 (3H, m); 13 C NMR (400
MHz, CDCl3): δ (ppm) 151.30, 149.34, 129.28, 127.52, 126.69, 124.12,
117.90, 116.28, 112.53, 107.17, 65.80, 59.01, 38.16, 37.58, 19.67; MS m/z =
252 (M + ); Anal. Calcd. for C17H20N2: C, 80.91; H, 7.99; N, 11.10. Found: C,
80.87; H, 8.01; N, 11.12.
N-[(2-METHYL-2, 3-DIHYDRO-1H-INDOL-1-YL) METHYL]-N-PHENYL
ANILINE (DNJ-207): IR (KBr, cm -1 ): 3230 (-NH), 3014 (Ar-H), 2988 (–CH3),
2850 (–CH2), 1550, 1502, 1473, 1460 (Ar-H), 1377 (C-N, Ar, 3°); MS m/z =
314 (M + ); Anal. Calcd. for C22H22N2: C, 84.04; H, 7.05; N, 8.91. Found: C,
84.08; H, 7.03; N, 8.89.
Department of Chemistry, Saurashtra University, Rajkot-360 005 56