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Chapter – 1 Preparation and Yield optimization.....
Anal. Calcd. for C14H22N2: C, 77.01; H, 10.16; N, 12.83. Found: C, 77.04; H,
10.15; N, 12.81.
N-[(2-METHYL-2, 3-DIHYDRO-1H-INDOL-1-YL) METHYL]-N-PROPYL
PROPAN-1-AMINE (DNJ-110): IR (KBr, cm -1 ): 3062 (Ar-H), 2962 (–CH3),
2864 (–CH2), 1562, 1499, 1470, 1458 (Ar-H), 1375 (C-N, Ar, 3°); MS m/z =
246 (M + ); Anal. Calcd. for C16H26N2: C, 77.99; H, 10.64; N, 11.37. Found: C,
78.01; H, 10.64; N, 11.35.
N-BUTYL-N-[(2-METHYL-2, 3-DIHYDRO-1H-INDOL-1-YL) METHYL]
BUTAN-1-AMINE (DNJ-111): IR (KBr, cm -1 ): 3062 (Ar-H), 2962 (–CH3), 2862
(–CH2), 1560, 1500, 1470, 1462 (Ar-H), 1374 (C-N, Ar, 3°); MS m/z = 274
(M + ); Anal. Calcd. for C18H30N2: C, 78.77; H, 11.02; N, 10.21. Found: C, 78.80;
H, 11.05; N, 10.19.
N-[(2-METHYL-2, 3-DIHYDRO-1H-INDOL-1-YL) METHYL] ANILINE (DNJ-
201): IR (KBr, cm -1 ): 3256 (-NH), 3049 (Ar-H), 2914 (–CH3), 2818 (–CH2),
1558, 1495 1470, 1458 (Ar-H), 1380 (C-N, Ar, 3°), 1333 (C-N, Ar, 2°); MS m/z
= 238 (M + ); Anal. Calcd. for C16H18N2: C, 80.63; H, 7.61; N, 11.75. Found: C,
80.65; H, 7.59; N, 11.75.
3-CHLORO-N-[(2-METHYL-2, 3-DIHYDRO-1H-INDOL-1-YL) METHYL]
ANILINE (DNJ-202): IR (KBr, cm -1 ): 3318 (-NH), 3047 (Ar-H), 2962 (–CH3),
2864 (–CH2), 1562, 1503, 1470, 1460 (Ar-H), 1377 (C-N, Ar, 3°), 1327 (C-N,
Ar, 2°), 898 (1,3-di sub.), 750 (C-Cl); MS m/z = 272 (M + ); Anal. Calcd. for
C16H17ClN2: C, 70.45; H, 6.28; N, 10.27. Found: C, 70.49; H, 6.24; N, 10.31.
N-[(2-METHYL-2, 3-DIHYDRO-1H-INDOL-1-YL) METHYL]-3-
(TRIFLUOROMETHYL) ANILINE (DNJ-203): IR (KBr, cm -1 ): 3346 (-NH),
3030 (Ar-H), 2965 (–CH3), 2887 (–CH2), 1609, 1508, 1489, 1450 (Ar-H), 1374
(C-N, Ar, 3°), 1329 (C-N, Ar, 2°), 993 (C-F), 855 (1,3-di sub.); 1 H NMR (400
MHz, CDCl3): δ (ppm) 1.29 (3H, m), 3.66 (2H, qt), 4.11 (1H, qt), 4.63 (2H, q),
4.90 (1H, s), 6.60 (1H, t), 6.74 (2H, m), 6.88 (2H, m), 7.07 (1H, m), 7.23 (2H,
m); 13 C NMR (400 MHz, CDCl3): δ (ppm) 171.34, 150.63, 147.66, 147.04,
Department of Chemistry, Saurashtra University, Rajkot-360 005 55