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M. Sharma et al. / European Journal of Medicinal Chemistry 46 (2011) 480e487
6.1.1. N,N0-dibenzyl-cyclohexane-1,2-diaminiumchloride (13)
Yield: 92%; Mp: 240 ꢁC; IR (KBr, cmꢃ1): 2946, 2715, 2641, 1624,
1458, 988, 754, 698, 508; 1H NMR (300 MHz, DMSO-d6):
10.23e9.93 (m, 4H), 7.69e7.38 (m, 10H), 4.27 (d, J ¼ 12 Hz, 2H), 4.12
(d, J ¼ 12 Hz, 2H), 3.75e3.58 (s, 2H), 2.30e2.27 (m, 2H), 1.85e1.75
(m, 4H), 1.18 (s, 2H); 13C NMR (75.5 MHz, DMSO-d6): 132.38, 131.28,
129.74, 129.36, 56.92, 48.40, 26.54, 23.10; ESI-HRMS calculated for
C20H28Cl2N2: 366.1630, Found: 294.2095 [M ꢃ 2HCl]þ; Anal. calcd.
for C20H28Cl2N2: C, 65.39; H, 7.68; N, 7.63; found: C, 65.40; H, 7.42;
N, 7.84.
2.64e2.56 (m, 2H), 2.32e2.29 (m, 2H), 1.78 (s, 4H), 1.18e1.11 (m,
14H); 13C NMR (75.5 MHz, DMSO-d6): 144.48, 144.68, 130.66,
130.49, 128.72, 127.93, 55.95, 48.49, 47.28, 27.90, 25.66, 22.23,
15.54; ESI-HRMS calculated for C26H40Cl2N2: 450.2569. Found:
378.3037 [M ꢃ 2HCl]þ; Anal. calcd. for C26H40Cl2N2: C, 69.16; H,
8.93; N, 6.20; Found: C, 69.28; H, 8.88; N, 6.34.
6.1.7. N,N0-Bis-(4-n-butyl-benzyl)-cyclohexane-1,2-diaminium
dichloride (19)
Yield: 82%; Mp: 200 ꢁC; IR (KBr, cmꢃ1): 2931, 2858, 2633, 1545,
1519, 1458, 1006, 828, 524; 1H NMR (300 MHz, DMSO-d6): 10.16
(brs, 2H), 9.84 (brs, 2H), 7.56 (d, J ¼ 9 Hz, 4H), 7.19 (d, J ¼ 9 Hz, 4H),
4.20 (d, J ¼ 12 Hz, 2H), 4.08 (d, J ¼ 12 Hz, 2H), 3.57 (s, 2H), 2.56 (t,
J ¼ 9 Hz, 4H), 2.31e2.28 (m, 2H), 1.90e1.73 (m, 4H), 1.33e1.20 (m,
6H), 1.56e1.44 (m, 4H), 0.86 (t, J ¼ 9 Hz, 6H); 13C NMR (75.5 M Hz,
DMSO-d6): 13.70, 20.62, 21.63, 21.67, 22.21, 22.77, 23.91, 25.66,
25.87, 29.17, 32.98, 34.99, 47.27, 48.37, 50.21, 55.46, 55.89, 57.36,
128.37, 128.66, 128.93, 130.44, 143.17, 143.35; ESI-HRMS m/z
[M]þ calculated for C28H44Cl2N2: 478.2882. Found: 406.3349
[M ꢃ 2HCl]þ; Anal. calcd. for C28H44Cl2N2: C, 70.13; H, 9.25; N, 5.84;
Found: C, 70.20; H, 9.22; N, 5.67.
6.1.2. N,N0-Bis-(2-methyl-benzyl)-cyclohexane-1,2-diaminium
dichloride (14)
Yield: 90%; Mp: 219 ꢁC; IR (KBr, cmꢃ1): 2942, 2865, 2717, 1646,
1560, 1464, 1319, 1038, 788, 753; 1H NMR (300 MHz, DMSO-d6):
10.13 (brs, 2H), 9.79 (brs, 2H), 7.69e7.67 (m, 2H), 7.30e7.19 (m, 6H),
4.29e4.19 (m, 4H), 3.81(s, 2H), 2.43e2.41 (m, 8H),1.27 (s, 2H),1.80 (s,
4H); 13C NMR (75.5 MHz, DMSO-d6): 138.50, 132.02, 131.24, 131.03,
129.82, 126.72, 57.88, 46.13, 41.24, 40.97, 40.41, 40.69, 40.13, 39.58,
26.92, 23.37, 20.18; ESI-HRMS calculated for C22H32Cl2N2: 394.1943,
Found: 322.2410 [M ꢃ 2HCl]þ; Anal. calcd. for C22H32Cl2N2: C, 66.83;
H, 8.16; N, 7.08; Found: C, 66.64; H, 8.28; N, 7.12.
6.1.8. N,N0-Bis-(4-tert-butyl-benzyl)-cyclohexane-1,2-diaminium
dichloride (20)
6.1.3. N,N0-Bis-(3-methyl-benzyl)-cyclohexane-1,2-diaminium
dichloride (15)
Yield: 90%; Mp: 244 ꢁC; IR (Film, cmꢃ1): 2930, 2853, 1682, 1641,
1588, 1513, 1460, 1420, 1267, 1026; 1H NMR (300 MHz, DMSO-d6):
10.06 (brs, 2H), 9.73 (brs, 2H), 7.57 (d, J ¼ 6 Hz, 4H), 7.41 (d, J ¼ 9 Hz,
4H), 4.20 (d, J ¼ 12 Hz, 2H), 4.08 (d, J ¼ 12 Hz, 2H), 3.57 (s, 2H),
2.35e2.31 (m, 2H), 1.75 (s, 4H), 1.28e1.24 (s, 20H); 13C NMR
(75.5 MHz, DMSO-d6): 151.50, 130.26, 128.61, 125.31, 59.04, 47.19,
34.37, 31.01, 25.64, 22.23; ESI-HRMS m/z [M]þ calculated for
C28H44Cl2N2: 478.2882, Found: 406.3350 [M ꢃ 2HCl]þ; Anal. calcd.
for C28H44Cl2N2: C, 70.13; H, 9.25; N, 5.84; Found: C, 70.24; H, 9.38;
N, 5.88.
Yield: 85%; Mp: 229 ꢁC; IR (Nujol, cmꢃ1): 2923, 2854, 2685, 2629,
1608, 1538, 1377, 1162, 803, 695; 1H NMR (300 MHz, DMSO-d6):
10.20 (brs, 2H), 9.87 (brs, 2H), 7.48e7.44 (m, 4H), 7.31e7.18 (m, 4H),
4.21 (d, J ¼ 12 Hz, 2H), 4.07 (d, J ¼ 12 Hz, 2H), 3.56 (s, 2H), 2.30 (s, 8H),
1.85e1.73 (m, 4H), 1.18 (s, 2 H); 13C NMR (75.5 MHz, DMSO-d6):
138.56, 132.28, 131.77, 130.33, 129.30, 128.28, 56.86, 48.34, 26.48,
23.09, 21.78; ESI-HRMS calculated for C22H32Cl2N2: 394.1943,
Found: 322.2408 [M ꢃ 2HCl]þ; Anal. calcd. for C22H32Cl2N2: C, 66.83;
H, 8.16; N, 7.08; Found: C, 66.85; H, 8.30; N, 7.15.
6.1.4. N,N0-Bis-(4-methyl-benzyl)-cyclohexane-1,2-diaminium
dichloride (16)
6.1.9. N,N0-Bis-(2-bromo-benzyl)-cyclohexane-1,2-diaminium
dichloride (21)
Yield: 89%; Mp: 247 ꢁC; IR (Nujol, cmꢃ1): 2924, 2854, 2709, 2637,
1542, 1376, 1248, 1002, 817, 745; 1H NMR (300 MHz, DMSO-d6):
10.02 (s, 2H), 9.85 (s, 2H), 7.53e7.50 (d, J ¼ 9 Hz, 4H), 7.21e7.18 (d,
J ¼ 9 Hz, 4H), 4.20 (d, J ¼ 12 Hz, 2H), 4.06 (d, J ¼ 12 Hz, 2H), 3.47 (s,
2H), 2.28 (s, 8H), 1.81e1.70 (m, 4H), 1.16e1.12 (s, 2H), 13C NMR
(75.5 MHz, DMSO-d6): 139.23, 131.24, 129.95, 129.25, 56.75, 48.10,
26.59, 23.13, 21.64; ESI-HRMS calculated for C22H32Cl2N2: 394.1943,
Found: 322.2412 [M ꢃ 2HCl]þ; Anal. calcd. for C22H32Cl2N2: C,
66.83; H, 8.16; N, 7.08; Found: C, 66.74; H, 8.34; N, 7.28.
Yield: 79%; Mp: 262 ꢁC; IR (Nujol, cmꢃ1): 2924, 2854, 2645,1521,
1376,1028, 805, 755, 670; 1H NMR (300 MHz, DMSO-d6): 10.25 (brs,
2H), 10.00 (brs, 2H), 7.97e7.93 (m, 2H), 7.69 (d, J ¼ 7.8 Hz, 2H),
7.38e7.33 (m, 2H), 7.48e7.43 (m, 2H), 4.47e4.27 (m, 4H), 3.73 (s,
2H), 2.41e2.38 (m, 2H), 2.05e1.80 (m, 4H), 1.29 (s, 2H); ESI-HRMS
m/z [M]þ calculated for C20H26Br2Cl2N2: 521.9840, Found: 450.0308
[M ꢃ 2HCl]þ, 452.0390 [M þ 2 ꢃ 2HCl]þ, 454.0267 [M þ 4 ꢃ 2HCl]þ;
Anal. calcd. for C20H26Br2Cl2N2: C, 45.74; H, 4.99; N, 5.33; Found: C,
45.68; H, 4.85; N, 5.50.
6.1.5. N,N0-Bis-(4-ethyl-benzyl)-cyclohexane-1,2-diaminium
dichloride (17)
6.1.10. N,N0-Bis-(3-bromo-benzyl)-cyclohexane-1,2-diaminium
dichloride (22)
Yield: 89%; Mp: 218 ꢁC; IR (KBr, cmꢃ1): 2932, 2717,1545,1461, 826;
1H NMR (300 MHz, DMSO-d6): 10.20 (brs, 2H), 9.83 (brs, 2H), 7.58 (d,
J ¼ 7.5 Hz, 4H), 7.25 (d, J ¼ 7.5 Hz, 4H), 4.22 (d, J ¼ 12.3 Hz, 2H), 4.09 (d,
J ¼ 12.3 Hz, 2H), 3.61 (s, 2H), 2.88(q, J ¼ 6.6 Hz, 4H), 2.34e2.31 (m, 2H),
1.88 (s, 4H), 1.16e1.18 (m, 8H); 13C NMR (75.5 MHz, DMSO-d6): 149.19,
130.77, 130.57, 128.89, 126.39, 55.95, 47.31, 33.20, 25.60, 23.74, 23.67,
22.20; ESI-HRMS calculated for C24H36Cl2N2: 422.2256, Found:
350.2773 [M ꢃ 2HCl]þ; Anal. calcd. for C24H36Cl2N2: C, 68.07; H, 8.57,
N, 6.62; Found: C, 68.20; H, 8.65, N, 6.54.
Yield: 85%; Mp: 242 ꢁC; IR (KBr, cmꢃ1): 2939, 2862, 2689, 2622,
1728, 1570, 1472, 1372, 1246, 1209; 1H NMR (300 MHz, DMSO-d6):
10.33 (brs, 2H), 9.92 (brs, 2H), 7.99e7.96 (m, 2H), 7.74e7.68 (m, 2H),
7.59e7.56 (m, 2H), 7.38e7.33 (m, 2H), 4.33 (d, J ¼ 12 Hz, 2H), 4.14 (d,
J ¼ 12 Hz, 2H), 3.63 (s, 2H), 2.28e2.32 (m, 2H), 1.97e1.76 (m, 4H),
1.20e1.13 (m, 2H); 13C NMR (75.5 MHz, DMSO-d6): 135.19, 133.95,
132.54,131.39,130.41,122.40, 60.59, 57.17, 47.75, 26.42, 23.02, 21.62,
14.94; ESI-HRMS m/z [M]þ calculated for C20H26Br2Cl2N2: 521.9840,
Found: 450.0310 [M ꢃ 2HCl]þ, 452.0388 [M þ 2 ꢃ 2HCl]þ, 454.0268
[M þ 4 ꢃ 2HCl]þ; Anal. calcd. for C20H26Br2Cl2N2: C, 45.74; H, 4.99;
N, 5.33; Found: C, 45.60; H, 4.78; N, 5.45.
6.1.6. N,N0-Bis-(4-isopropyl-benzyl)-cyclohexane-1,2-diaminium
dichloride (18)
Yield: 86%; Mp: 232 ꢁC; IR (KBr, cmꢃ1): 2959, 2870, 2714, 2631,
1579, 1517, 1461, 1363, 1267, 822; 1H NMR (300 MHz, DMSO-d6):
10.05 (brs, 2H), 9.80 (brs, 2H), 7.55 (d, J ¼ 9 Hz, 4H), 7.23 (d, J ¼ 9 Hz,
4H), 4.22 (d, J ¼ 15 Hz, 2H), 4.08 (d, J ¼ 15 Hz, 2H), 3.53 (s, 2H),
6.1.11. N,N0-Bis-(4-bromo-benzyl)-cyclohexane-1,2-diaminium
dichloride (23)
Yield: 92%; Mp: 242 ꢁC; IR (Nujol, cmꢃ1): 2924, 2854, 2630,
1594, 1543, 1488, 1377, 1072, 1013, 808; 1H NMR (300 MHz,