Med Chem Res
+
1
-(Piperazin-1-ylmethyl)-2-(5-p-tolyl-4,5-dihydro-1H-
of piperidine), 25.6 (CH ). EI-MS m/z: 373 (M ). Anal.
3
pyrazol-3-yl)-1H-benzimidazole (5d)
calcd for C H N : C, 73.96; H, 7.29; N, 18.75. Found: C,
2
3 27 5
74.19; H, 7.28; N, 18.70.
−
1
Yield = 79%, m.p. 239–240 °C. IR (KBr) cm : 3342 &
3
1
1
255 (NH), 3056 (Ar-CH), 2953 (CH –CH), 1648 (C=N),
N,N-Dimethyl(2-(5-phenyl-4,5-dihydro-1H-pyrazol-3-yl)-
1H-benzimidazol-1-yl)methanamine (5g)
3
1
620 (C=C). H-NMR (CDCl , 500 MHz) δ ppm: 1.70 (s,
3
H, NH of piperazine), 2.13 (d, 2H, CH of pyrazole), 2.36
2
−
1
(
s, 3H, CH ), 2.95–3.61 (m, 8H, CH of piperazine), 4.02 (t,
Yield = 76%, m.p. 222–223 °C. IR (KBr) cm : 3356
3
2
1
H, CH of pyrazole), 4.94 (s, 2H, CH ), 6.67 (s, 1H, NH of
(NH), 3065 (Ar-CH), 2932 (CH –CH), 1637 (C=N), 1613
2
3
1
3
1
pyrazole), 6.85–8.08 (m, 8H, Ar-CH). C-NMR (CDCl3,
(C=C). H-NMR (CDCl , 500 MHz) δ ppm: 1.89 (s, 6H, N
3
5
1
00 MHz) δ ppm: 157.6 (C-3 of pyrazole), 142.8 (C-2),
40.5 (C′-1), 137.9 (C-9), 133.1 (C′-4), 129.2 (C-8), 124.3
(CH ) ), 2.09 (d, 2H, CH of pyrazole), 4.20 (t, 1H, CH of
3
2
2
pyrazole), 4.73 (s, 2H, CH ), 6.61 (s, 1H, NH of pyrazole),
2
1
3
(
1
C′-3 & C′-5), 121.2 (C′-2 & C′-6), 114.0 (C-5 & C-6),
10.4 (C-4 & C-7), 70.2 (CH ), 54.9 (C-2 & C-6 of
6.95–7.84 (m, 9H, Ar-CH). C-NMR (CDCl , 500 MHz) δ
3
ppm: 159.2 (C-3 of pyrazole), 143.7 (C-2), 139.8 (C′-1),
137.9 (C-9), 133.1 (C′-4), 131.6 (C-8), 126.5 (C′-3 & C′-5),
124.0 (C′-2 & C′-6), 119.4 (C-5 & C-6), 115.6 (C-4 & C-7),
2
piperazine), 51.0 (C-5 of pyrazole), 48.3 (C-3 & C-5 of
piperazine), 43.7 (C-4 of pyrazole), 25.4 (CH ). EI-MS m/z:
3
+
3
74 (M ). Anal. calcd for C H N : C, 70.56; H, 7.00; N,
68.1 (CH ), 46.8 (C-5 of pyrazole), 39.3 (C-4 of pyrazole),
2
2
26
6
2
+
2
2.44. Found: C, 70.21; H, 7.02; N, 22.49.
42.5 (N(CH ) ). EI-MS m/z: 319 (M ). Anal. calcd for
3
2
C H N : C, 71.45; H, 6.63; N, 21.93. Found: C, 71.70; H,
1
9 21 5
1
-(Morpholinomethyl)-2-(5-p-tolyl-4,5-dihydro-1H-
6.61; N, 21.87.
pyrazol-3-yl)-1H-benzimidazole (5e)
N-Ethyl-N-((2-(5-phenyl-4,5-dihydro-1H-pyrazol-3-yl)-1H-
benzimidazol-1-yl)methyl)ethanamine (5h)
−
1
Yield = 73%, m.p. 196–198 °C. IR (KBr) cm : 3329
(
(
NH), 3081 (Ar-CH), 2956 (CH –CH), 1640 (C=N), 1622
3
1
Yield = 73%, m.p. 256–258 °C. IR (KBr) cm−1: 3333
C=C), 1095 (C-O-C). H-NMR (CDCl , 500 MHz) δ ppm:
3
2
.06 (d, 2H, CH of pyrazole), 2.72 (s, 3H, CH ), 2.81–3.47
(NH), 3079 (Ar-CH), 2951 (CH –CH), 1644 (C=N), 1618
2
3
3
1
(
m, 8H, CH of morpholine), 4.28 (t, 1H, CH of pyrazole),
(C=C). H-NMR (CDCl , 500 MHz) δ ppm: 1.76 (t, 6H,
2
3
4
.65 (s, 2H, CH ), 6.89 (s, 1H, NH of pyrazole), 7.20–8.13
CH ), 2.31 (d, 2H, CH of pyrazole), 2.98 (t, 4H, CH ),
2
3
2
2
1
3
(
m, 8H, Ar-CH). C-NMR (CDCl , 500 MHz) δ ppm:
4.07 (t, 1H, CH of pyrazole), 4.82 (s, 2H, CH ), 6.95 (s, 1H,
2
3
1
3
1
58.0 (C-3 of pyrazole), 146.2 (C-2), 137.8 (C′-1), 132.0
NH of pyrazole), 7.33–8.14 (m, 9H, Ar-CH). C-NMR
(
(
(
C-9), 130.2 (C′-4), 123.5 (C-8), 122.3 (C′-3 & C′-5), 119.1
C′-2 & C′-6), 114.8 (C-5 & C-6), 108.7 (C-4 & C-7), 71.5
(CDCl , 500 MHz) δ ppm: 158.8 (C-3 of pyrazole), 144.5
(C-2), 139.7 (C′-1), 135.5 (C-9), 132.7 (C′-4), 129.3 (C-8),
126.4 (C′-3 & C′-5), 118.6 (C′-2 & C′-6), 114.2 (C-5 & C-
3
CH ), 68.3 (C-3 & C-5 of morpholine), 53.8 (C-2 & C-6 of
2
morpholine), 49.6 (C-5 of pyrazole), 40.9 (C-4 of pyrazole),
6), 111.0 (C-4 & C-7), 70.4 (CH ), 48.9 (C-5 of pyrazole),
2
+
2
6.1 (CH ). EI-MS m/z: 375 (M ). Anal. calcd for
38.1 (C-4 of pyrazole), 45.2 (N(CH CH ) ), 17.6 (N
3
2
3 2
+
C H N O: C, 70.38; H, 6.71; N, 18.65. Found: C, 70.16;
(CH CH ) ). EI-MS m/z: 347 (M ). Anal. calcd for
2 3 2
2
2
25
5
H, 6.72; N, 18.71.
C H N : C, 72.59; H, 7.25; N, 20.16. Found: C, 72.81; H,
21 25 5
7.24; N, 20.11.
1
-(Piperidin-1-ylmethyl)-2-(5-p-tolyl-4,5-dihydro-1H-
pyrazol-3-yl)-1H-benzimidazole (5f)
N-Phenyl-N-((2-(5-phenyl-4,5-dihydro-1H-pyrazol-3-yl)-
H-benzimidazol-1-yl)methyl)benzenamine (5i)
1
−
1
Yield = 81%, m.p. 245–246 °C. IR (KBr) cm : 3368
−
1
(
(
NH), 3044 (Ar-CH), 2922 (CH –CH), 1643 (C=N), 1631
Yield = 72%, m.p. 235–236 °C. IR (KBr) cm : 3368
3
1
C=C). H-NMR (CDCl , 500 MHz) δ ppm: 1.92–2.69 (m,
(NH), 3043 (Ar-CH), 2935 (CH –CH), 1636 (C=N), 1612
3
3
1
1
0H, CH of piperidine), 2.82 (d, 2H, CH of pyrazole),
(C=C). H-NMR (CDCl , 500 MHz) δ ppm: 2.17 (d, 2H,
2
2
3
3
.04 (s, 3H, CH ), 4.16 (t, 1H, CH of pyrazole), 4.87 (s, 2H,
CH of pyrazole), 4.10 (t, 1H, CH of pyrazole), 4.92 (s, 2H,
3
2
CH ), 6.78 (s, 1H, NH of pyrazole), 7.03–8.21 (m, 8H, Ar-
CH ), 6.76 (s, 1H, NH of pyrazole), 7.13–8.54 (m, 19H, Ar-
2
2
1
3
13
CH). C-NMR (CDCl , 500 MHz) δ ppm: 163.7 (C-3 of
CH). C-NMR (CDCl , 500 MHz) δ ppm: 162.4 (C-3 of
3
3
pyrazole), 145.7 (C-2), 140.1 (C′-1), 136.9 (C-9), 131.3
pyrazole), 147.3 (C-2), 145.1 (C-1 of phenyl), 142.4 (C′-1),
141.7 (C-3 & C-5 of phenyl), 140.1 (C-9), 136.9 (C′-4),
133.6 (C-8), 132.4 (C′-3 & C′-5), 126.0 (C′-2 & C′-6),
122.7 (C-5 & C-6), 120.5 (C-2 & C-6 of phenyl), 119.6 (C-
(
C′-4), 129.4 (C-8), 127.2 (C′-3 & C′-5), 120.6 (C′-2 &
C′-6), 115.8 (C-5 & C-6), 112.6 (C-4 & C-7), 73.2 (CH2),
5.1 (C-2 & C-6 of piperidine), 50.3 (C-5 of pyrazole), 41.0
C-4 of pyrazole), 29.4 (C-4 of piperidine), 28.7 (C-3 & C-5
5
(
4 of phenyl), 117.5 (C-4 & C-7), 73.7 (CH ), 50.2 (C-5 of
2