208 JOURNAL OF CHEMICAL RESEARCH 2015
238). Anal. calcd for C24H22ClFN4: C, 68.48; H, 5.27; N, 13.31; found: C,
68.44; H, 5.23; N, 13.24%. ESI-MS: 423.30, 421.27 [M+1]+.
34.78, 49.01 (2CH2), 51.60 (2CH2), 116.01 (2C), 119.50, 122.12, 128.36,
129.42 (2C), 129.81, 129.88, 131.05, 131.92, 136.30, 140.83, 141.07, 151.44
(C=N), 153.66 (d, J=240). Anal. calcd for C24H22BrFN4: C, 61.94; H, 4.77;
N, 12.04; found: C, 61.88; H, 4.69; N, 11.97%. ESI-MS: 467.19 [M+2]+,
465.30 [M]+.
5-Fluoro-2-(3-methylbenzyl)-6-(4-phenylpiperazin-1-yl)-1H-
benzimidazole (17): 1H NMR (400 MHz, DMSO-d6) δ 2.24 (s, 3H), 3.09
(m, 4H), 3.27 (m, 4H), 4.07 (s, 2H), 6.79 (t, J=6.8, 1H), 6.96–7.29 (m,
10H), 12.20 (s, 1H). 13C NMR (100 MHz, DMSO-d6) δ 21.43, 35.33, 49.02
(2CH2), 51.63 (2CH2), 116.01 (2C), 119.50, 126.24, 127.52, 127.59, 128.82
(2C), 129.42 (2C), 129.75 (2C), 136.32, 137.94, 138.22, 151.45 (C=N),
153.12 (d, J=240). Anal. calcd for C25H25FN4: C, 74.97; H, 6.29; N, 13.99;
found: C, 74.89; H, 6.21; N, 13.90%. ESI-MS: 401.29 [M+1]+.
5-Fluoro-2-(4-bromobenzyl)-6-(4-phenylpiperazin-1-yl)-1H-
benzimidazole (9): 1H NMR (400 MHz, DMSO-d6) δ 3.09 (m, 4H), 3.29
(m, 4H), 4.18 (s, 2H), 6.79 (t, J=7.2, 1H), 6.99 (d, J=8.4, 2H), 7.14–7.36 (m,
6H), 7.51 (d, J=8.4, 2H). 13C NMR (100 MHz, DMSO-d6) δ 34.06, 48.98
(2CH2), 51.51 (2CH2), 103.60, 116.03 (2C), 119.53, 120.38, 129.41 (2C),
131.53 (2C), 131.86 (2C), 136.79, 136.87, 137.00, 151.39 (C=N), 153.56 (d,
J= 238). Anal. calcd for C24H22BrFN4: C, 61.94; H, 4.77; N, 12.04; found:
C, 61.90; H, 4.72; N, 12.01%. ESI-MS: 467.29 [M+2]+, 465.26 [M]+.
5-Fluoro-2-(4-methoxybenzyl)-6-(4-phenylpiperazin-1-yl)-1H-
benzimidazole (10): 1H NMR (400 MHz, DMSO-d6) δ 3.08 (m, 4H), 3.27
(m, 4H), 3.69 (s, 3H), 4.06 (s, 2H), 6.79 (t, J=7.2, 1H), 6.89 (d, J=8.4, 2H),
6.97 (d, J=8.0, 2H), 7.20-7.31 (m, 6H), 12.15 (br, 1H). 13C NMR (100 MHz,
DMSO-d6) δ 34.53, 49.02 (2CH2), 51.64 (2CH2), 55.47, 114.30, 114.33
(2C), 116.01 (2C), 119.50, 129.41 (2C), 130.00, 130.20 (2C), 136.26, 151.45
(C=N), 153.15 (d, J=240), 158.44. Anal. calcd for C25H25FN4O: C, 72.09;
H, 6.05; N, 13.45; found: C, 72.03; H, 6.01; N, 13.38%. ESI-MS: 417.32
[M+1]+.
5-Fluoro-2-(4-nitrobenzyl)-6-(4-phenylpiperazin-1-yl)-1H-
benzimidazole (11): 1H NMR (400 MHz, DMSO-d6) δ 3.09 (m, 4H), 3.27
(m, 4H), 4.30 (s, 2H), 6.78 (t, J=6.8, 1H), 6.97 (d, J=7.6, 2H), 7.19–7.25 (m,
4H), 7.57 (d, J=8.4, 2H), 8.18 (d, J=8.8, 2H), 12.31 (br, 1H). 13C NMR (100
MHz, DMSO-d6) δ 34.95, 48.99 (2CH2), 51.57 (2CH2), 100.05, 115.99,
116.02 (2C), 119.45, 124.02 (2C), 129.40 (2C), 130.53 (2C), 146.05, 146.74,
151.42 (C=N), 152.98 (d, J=238). Anal. calcd for C24H22FN5O2: C, 66.81;
H, 5.14; N, 16.23; found: C, 66.75; H, 5.10; N, 16.17%. ESI-MS: 432.29
[M+1]+.
Received 14 February 2015; accepted 27 February 2015
Paper 1503202 doi: 10.3184/174751915X14268750943001
Publsihed online: 13 April 2015
References
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5-Fluoro-2-(4-methylbenzyl)-6-(4-phenylpiperazin-1-yl)-1H-
benzimidazole (12): 1H NMR (400 MHz, DMSO-d6) δ 2.23 (s, 3H), 3.09
(m, 4H), 3.28 (m, 4H), 4.36 (s, 2H), 6.78 (t, J=6.8, 1H), 6.98 (d, J=8.0,
2H), 7.10 (d, J=7.6, 2H), 7.16–7.24 (m, 6H), 12.13 (br, 1H). 13C NMR (100
MHz, DMSO-d6) δ 21.05, 34.95, 49.01 (2CH2), 51.63 (2CH2), 116.00,
116.03, 119.48, 129.00, 129.01, 129.40, 129.43, 129.48, 135.03, 135.15,
135.87, 135.95, 151.44 (C=N), 154.53 (d, J=236). Anal. calcd for
C25H25FN4: C, 74.97; H, 6.29; N, 13.99; found: C, 74.92; H, 6.25; N,
13.95%. ESI-MS: 401.29 [M+1]+.
8
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1
benzimidazole (13): H NMR (400 MHz, DMSO-d6) δ 3.08 (m, 4H),
3.26 (m, 4H), 4.16 (s, 2H), 6.78 (t, J=7.2, 1H), 6.96 (d, J=8.0, 2H), 7.15
(d, J=8.0, 1H), 7.22 (t, J=8.0, 2H), 7.26–7.33 (m, 2H), 7.54 (d, J=8.0,
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5-Fluoro-2-(3-fluorobenzyl)-6-(4-phenylpiperazin-1-yl)-1H-
benzimidazole (14): 1H NMR (400 MHz, DMSO-d6) δ 3.09 (m, 4H), 3.27
(m, 4H), 4.17 (s, 2H), 6.78 (t, J=6.8, 1H), 6.96 (d, J=5.6, 2H), 7.02–7.33
(m, 8H), 12.20 (br, 1H). 13C NMR (100 MHz, DMSO-d6) δ 34.94, 49.01
(2CH2), 51.61 (2CH2), 113.68, 113.88, 115.89, 116.01 (2C), 116.11, 119.50,
125.32 (2C), 129.41 (2C), 130.78 (d, J=8.6), 136.41 (d, J=11.0), 140.82,
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Anal. calcd for C24H22F2N4: C, 71.27; H, 5.48; N, 13.85; found: C, 71.20; H,
5.42; N, 13.81%. ESI-MS: 405.24 [M+1]+.
5-Fluoro-2-(3-chlorobenzyl)-6-(4-phenylpiperazin-1-yl)-1H-
benzimidazole (15): 1H NMR (400 MHz, DMSO-d6) δ 3.09 (m, 4H), 3.27
(m, 4H), 4.17 (s, 2H), 6.79 (t, J=7.2, 1H), 6.96 (d, J=7.6, 2H), 7.19–7.39
(m, 8H), 12.25 (br, 1H). 13C NMR (100 MHz, DMSO-d6) δ 34.85, 49.02
(2CH2), 51.60 (2CH2), 116.01 (2C), 119.50, 126.92, 127.96, 129.07, 129.41
(2C), 129.68, 130.72, 133.50, 136.35, 140.53, 151.44 (C=N), 152.94 (d, J=
236), 153.66. Anal. calcd for C24H22ClFN4: C, 68.48; H, 5.27; N, 13.31;
found: C, 68.41; H, 5.19; N, 13.22%. ESI-MS: 423.34, 421.31 [M+1]+.
5-Fluoro-2-(3-bromobenzyl)-6-(4-phenylpiperazin-1-yl)-1H-
benzimidazole (16): 1H NMR (400 MHz, DMSO-d6) δ 3.09 (m, 4H), 3.27
(m, 4H), 4.15 (s, 2H), 6.78 (t, J=6.8, 1H), 6.97 (d, J=7.8, 2H), 7.20–7.42
(m, 7H), 7.53 (s, 1H), 12.25 (br, 1H). 13C NMR (100 MHz, DMSO-d6) δ
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