(not final pg. №)
B. R. RAO et al.: Synthesis of Novel Benzamide- piperazine-sulfonamide Hybrids …
5
δ/ppm: 3.06–3.23(m, 4H, piperzinyl H), 3.56–3.68(m, 2H,
piperzinyl H), 3.76–3.87 (m, 2H, piperzinyl H), 4.23 (d, 2H, J
= 3.8 Hz, COCH2NH), 7.12–7.22 (m, 2H, Ar–H), 7.40–7.48 (m,
2H, Ar–H), 7.48–7.59 (m, 3H, Ar–H), 7.63–7.70 (m, 1H, Ar–
H), 7.76–7.87 (m, 2H, Ar–H); 13C NMR (75 MHz, CDCl3)
δ/ppm: 41.2, 41.9, 43.2, 45.2, 45.7, 116.5, 126.5, 126.8,
128.5, 129.1, 134.0, 166.8, 167.6; ESI-MS m/z: 395 (M+1)+,
417 (M+23)+. Anal. Calcd for C17H19N3O4S2: C, 51.90; H, 4.87;
N, 10.69. Found: C, 51.66; H, 4.72; N, 10.54.
MHz, CDCl3) δ/ppm: 1.35 (s, 9H, 3 x CH3), 3.03–3.12 (m, 4H,
piperzinyl H), 3.57 (m, 2H, piperzinyl H), 3.77 (m, 2H,
piperzinyl H), 4.18 (d, 2H, J = 3.3 Hz, COCH2NH), 7.07–7.13
(m, 2H, Ar–H), 7.53–7.58 (m, 2H, Ar–H), 7.64–7.69 (m, 2H,
Ar–H), 7.78–7.83 (m, 3H, Ar–H); 13C NMR (75 MHz, CDCl3)
δ/ppm: 31.0, 35.3, 41.5, 42.0, 43.2, 45.5, 45.8, 117.0, 125.2,
126.6, 127.1, 128.3, 131.5, 135.1, 148.2, 162.3, 166.9,
167.7; ESI-MS m/z: 462 (M+1)+, 484 (M+23)+. Anal. Calcd for
C23H29FN3O4S: C, 59.72; H, 6.32; N, 9.09. Found: C, 59.65; H,
6.21; N, 9.00.
N-(2-(4-((4-bromophenyl)sulfonyl)piperazin-1-yl)-2-oxo-
ethyl)benzamide (3j)
4-fluoro-N-(2-(4-((4-methoxyphenyl)sulfonyl)piperazin-1-
yl)-2-oxoethyl)benzamide (4d)
White solid. Yield: 81 %; mp: 154–156 °C; IR (KBr) ṽ/cm−1:
1
1156, 1632, 2850, 2914, 3075, 3412; H NMR (400 MHz,
White solid. Yield: 76.5 %; mp: 123–125 °C; IR (KBr)
ṽ/cm−1: 1155, 1623, 1662, 2854, 2924, 3097, 3299; 1H
NMR (300 MHz, CDCl3) δ/ppm : 2.97–3.12 (m, 4H,
piperzinyl H), 3.52–3.63 (m, 2H, piperzinyl H), 3.72–3.83
(m, 2H, piperzinyl H), 3.88 (s, 3H, Ph–OCH3), 4.17 (d, 2H, J
= 4.5 Hz, COCH2NH), 6.97–7.19 (m, 5H, Ar–H), 7.65–7.73
(m, 2H, Ar–H), 7.77–7.86 (m, 1H, Ar–H); 13C NMR (125
MHz, CDCl3) δ/ppm: 41.4, 41.6, 43.9, 45.7, 45.9, 55.7,
115.5, 115.8, 129.3, 129.4, 129.9, 134.2, 163.4, 166.1,
166.5; ESI-MS m/z: 458 (M+1)+, 480 (M+23)+. Anal. Calcd
for C20H22FN3O5S: C, 55.16; H, 5.10; N, 9.65. Found: C,
55.02; H, 5.02; N, 9.43.
CDCl3) δ/ppm: 3.00–3.11 (m, 4H, piperzinyl H), 3.42–3.49
(m, 2H, piperzinyl H), 3.62–3.67 (m, 2H, piperzinyl H), 4.20
(d, 2H, J = 4.2 Hz, COCH2NH), 7.14–7.20 (m, 1H, Ar–H), 7.21–
7.29 (m, 2H, Ar–H), 7.40–7.54 (m, 3H, Ar–H), 7.74–7.83 (m,
4H, Ar–H); 13C NMR (75 MHz, CDCl3) δ/ppm: 41.1, 41.5,
44.0, 45.2, 45.5, 116.4, 126.7, 128.1, 128.5, 129.4, 130.2,
133.6, 166.5, 167.1; ESI-MS m/z: 467 (M+1) +. Anal. Calcd
for C19H20BrN3O4S: C, 48.92; H, 4.33; N, 9.01. Found: C,
48.72; H, 4.21; N, 8.89.
4-fluoro-N-(2-oxo-2-(4-(phenylsulfonyl)piperazin-1-yl)-
ethyl)benzamide (4a)
White solid. Yield: 79 %; mp: 154-156 °C; IR (KBr) ṽ/cm−1:1164,
1649, 2855, 2922, 2998, 3067, 3413; 1H NMR (300 MHz,
CDCl3) δ/ppm: 3.01–3.16 (m, 4H, piperzinyl H), 3.54−3.65 (m,
2H, piperzinyl H), 3.73–3.83 (m, 2H, piperzinyl H), 4.17 (d, 2H,
J = 4.5 Hz, COCH2NH), 7.07–7.19 (m, 3H, Ar–H), 7.53–7.67 (m,
3H, Ar–H), 7.73–7.89 (m, 4H, Ar–H); 13C NMR (75 MHz, CDCl3)
δ/ppm: 41.2, 41.5, 43.4, 45.6, 45.9, 116.8, 125.3, 127.6, 128.2,
130.6, 130.9, 132.5, 163.5, 165.9, 167.2; ESI-MS m/z: 406
(M+1)+, 428 (M+23)+. Anal. Calcd for C19H20FN3O4S: C, 56.28;
H, 4.98; N, 10.37. Found: C, 56.12; H, 4.82; N, 10.19.
4-fluoro-N-(2-(4-((4-fluorophenyl)sulfonyl)piperazin-1-yl)-
2-oxoethyl)benzamide (4e)
White solid. Yield: 79 %; mp: 161–163 °C; IR (KBr) ṽ/cm−1
:
1
1162, 1638, 1657, 2864, 2921, 3068, 3412; H NMR (300
MHz, CDCl3) δ/ppm: 3.01–3.13 (m, 4H, piperzinyl H),
3.55–3.62 (m, 2H, piperzinyl H), 3.74–3.83 (m, 2H,
piperzinyl H), 4.18 (d, 2H, J = 3.9 Hz, COCH2NH), 7.06–
7.15 (m, 3H, Ar–H), 7.23–7.29 (m, 2H, Ar–H), 7.75–7.85
(m, 4H, Ar–H); 13C NMR (75 MHz, CDCl3) δ/ppm: 41.4,
41.6, 43.9, 45.6, 45.8, 115.5, 115.8, 116.5, 116.8, 129.3,
129.4, 130.3, 130.4, 134.5, 163.2, 163.8, 166.1, 166.5;
ESI-MS m/z: 424 (M+1)+, 446 (M+23)+. Anal. Calcd for
C19H19F2N3O4S: C, 53.89; H, 4.53; N, 9.93. Found: C, 53.62;
H, 4.36; N, 9.71.
4-fluoro-N-(2-oxo-2-(4-tosylpiperazin-1-yl)ethyl)benz-
amide(4b)
White solid. Yield:77 %; mp: 127–129 °C; IR (KBr) ṽ/cm−1:
1159, 1669, 1645, 2854, 2924, 3392; 1H NMR (400 MHz,
CDCl3) δ/ppm: 2.37 (s, 3H, Ph–CH3), 2.90–3.04 (m, 4H,
piperzinyl H), 3.49 (m, 2H, piperzinyl H), 3.70 (m, 2H,
piperzinyl H), 4.10 (d, 2H, J = 2.7 Hz, COCH2NH), 6.99–7.08 (m,
2H, Ar–H), 7.28–7.31 (m, 2H, Ar–H), 7.53–7.60 (m, 2H, Ar–H),
7.70–7.78 (m, 3H, Ar–H);13C NMR (75 MHz, CDCl3) δ/ppm:
21.3, 41.5, 41.7, 43.2, 45.1, 45.5, 115.9, 126.6, 127.6, 128.3,
128.9, 130.5, 135.4, 163.8, 166.9, 167.5; ESI-MS m/z: 420
(M+1)+, 342 (M+23)+. Anal. Calcd for C20H22FN3O4S: C, 57.26;
H, 5.29; N, 10.02. Found: C, 57.08; H, 5.15; N, 9.93.
4-fluoro-N-(2-oxo-2-(4-((4-(trifluoromethyl)phenyl)sulfo-
nyl)piperazin-1-yl)ethyl)benzamide (4f)
White solid. Yield: 82 %; mp: 155–157 °C; IR (KBr) ṽ/cm−1:
1
1161, 1213, 1629, 1653, 2857, 2924, 3403; H NMR (300
MHz, CDCl3) δ/ppm: 3.04–3.15 (m, 4H, piperzinyl H), 3.56–
3.64 (m, 2H, piperzinyl H), 3.76–3.83 (m, 2H, piperzinyl H),
4.20 (d, 2H, J = 3.8 Hz, COCH2NH), 7.06–7.16 (m, 3H, Ar–H),
7.35–7.42 (m, 2H, Ar–H), 7.77–7.85 (m, 3H, Ar–H); 13C NMR
(75 MHz, CDCl3) δ/ppm: 41.5, 41.6, 43.9, 45.6, 45.8, 116.8,
126.4, 126.5, 126.9, 128.1, 128.5, 131.8, 133.5, 164.1,
166.6, 167.1; ESI-MS m/z: 474 (M+1)+, 496 (M+23)+. Anal.
Calcd for C20H19F4N3O4S: C, 50.73; H, 4.05; N, 8.88. Found:
C, 50.55; H, 3.95; N, 8.62.
N-(2-(4-((4-(tert-butyl)phenyl)sulfonyl)piperazin-1-yl)-2-
oxoethyl)-4-fluorobenzamide(4c)
White solid. Yield: 87 %; mp: 114–116 °C; IR (KBr) ṽ/cm−1:
1
1166, 1650, 1674, 2925, 2961, 3099, 3304; H NMR (300
DOI: 10.5562/cca3535
Croat. Chem. Acta 2019, 92(3)