1.85 – 1.60 (m, 4H). 13C NMR (75 MHz, CDCl3) δ 173.92, 169.22, 151.42, 132.29, 131.42 (d, JCF=31.90 Hz),
129.49, 128.86, 127.77, 124.59, 124.23 (dd, JCF=272.74 Hz), 118.67, 115.73 (dd, JCF=3.75 Hz), 112.14 (dd,
JCF=3.75 Hz), 58.24, 53.00, 48.46, 43.34, 27.76, 24.52.
N-(5-Phenyl-1,2,4-oxadiazol-3-yl)-4-(4-(4-chlorophenyl)piperazin-1-yl)butan-1-amine (9e)
Compound 9e was prepared as white solid from 8e and benzoic acid. Yield: 32.3%. 1H NMR (300 MHz, CDCl3) δ
7.96 (d, J = 7.2 Hz, 2H), 7.54 (t, J = 7.3 Hz, 1H), 7.45 (t, J = 7.5 Hz, 2H), 7.21 (d, J = 9.0 Hz, 2H), 6.86 (d, J = 9.0
Hz, 2H), 5.74 (s, 1H), 3.39 – 3.19 (m, 6H), 2.81 – 2.54 (m, 4H), 2.46 (t, J = 6.6 Hz, 2H), 1.90 – 1.48 (m, 4H). 13C
NMR (75 MHz, CDCl3) δ 173.87, 169.19, 149.96, 132.31, 128.89, 128.84, 127.77, 124.55, 124.46, 117.24, 58.29,
53.04, 48.89, 43.33, 27.78, 24.54.
N-(5-(4-Chlorophenyl)-1,2,4-oxadiazol-3-yl)-4-(4-(2,4-dichlorophenyl)piperazin-1-yl)butan-1-amine (9f)
Compound 9f was prepared as colorless solid from 8c and 4-chlorobenzoic acid. Yield: 38.4%. Mp: 120-122 °C. 1H
NMR (300 MHz, CDCl3) δ 8.06 – 7.89 (m, 2H), 7.54 – 7.40 (m, 2H), 7.37 (d, J = 2.4 Hz, 1H), 7.17 (dd, J = 8.6, 2.4
Hz, 1H), 6.99 (d, J = 8.6 Hz, 1H), 5.81 (s, 1H), 3.32 (s, 2H), 3.12 (s, 4H), 2.67 (s, 4H), 2.48 (t, J = 6.6 Hz, 2H), 1.85
– 1.60 (m, 4H). 13C NMR (75 MHz, CDCl3) δ 172.94, 169.20, 148.03, 138.68, 130.26, 129.42, 129.26, 129.08,
128.14, 127.53, 123.06, 121.15, 77.42, 77.00, 76.57, 58.21, 53.20, 50.91, 43.35, 27.73, 24.54.
N-(5-(3-Chlorophenyl)-1,2,4-oxadiazol-3-yl)-4-(4-(2,4-dichlorophenyl)piperazin-1-yl)butan-1-amine (9g)
Compound 9g was prepared as colorless liquid from 8c and 3-chlorobenzoic acid. Yield: 35.7%. 1H NMR (300 MHz,
CDCl3) δ 8.01 (t, J = 1.7 Hz, 1H), 7.90 (d, J = 7.7 Hz, 1H), 7.60 – 7.47 (m, 1H), 7.47 – 7.30 (m, 2H), 7.18 (dd, J =
8.6, 2.4 Hz, 1H), 7.00 (d, J = 8.6 Hz, 1H), 6.01 (s, 1H), 3.31 (d, J = 4.2 Hz, 2H), 3.13 (s, 4H), 2.68 (s, 4H), 2.48 (t, J
= 6.5 Hz, 2H), 1.88 – 1.56 (m, 4H). 13C NMR (75 MHz, CDCl3) δ 172.57, 169.20, 148.03, 134.99, 132.33, 130.24,
129.40, 128.15, 127.76, 127.63, 126.22, 125.85, 121.14, 58.30, 53.22, 50.89, 43.37, 38.58, 27.82, 24.60.
N-(5-(2-Chlorophenyl)-1,2,4-oxadiazol-3-yl)-4-(4-(2,4-dichlorophenyl)piperazin-1-yl)butan-1-amine (9h)
Compound 9h was prepared as colorless liquid from 8c and 2-chlorobenzoic acid. Yield: 36.6%. 1H NMR (300 MHz,
CDCl3) δ 7.96 (dd, J = 7.8, 1.7 Hz, 1H), 7.49 (dtd, J = 9.8, 8.1, 1.6 Hz, 2H), 7.41 – 7.30 (m, 2H), 7.14 (dd, J = 8.6,
2.4 Hz, 1H), 6.98 (d, J = 8.6 Hz, 1H), 5.87 (s, 1H), 3.33 (t, J = 6.1 Hz, 2H), 3.12 (t, J = 4.4 Hz, 4H), 2.68 (s, 4H),
2.49 (t, J = 6.6 Hz, 2H), 1.84 – 1.57 (m, 4H). 13C NMR (75 MHz, CDCl3) δ 172.33, 168.96, 147.99, 133.51, 132.71,
131.51, 131.31, 130.21, 129.39, 128.11, 127.53, 126.90, 123.88, 121.27, 58.17, 53.19, 50.89, 43.34, 27.68, 24.50.
N-(5-(4-Methoxylphenyl)-1,2,4-oxadiazol-3-yl)-4-(4-(2,4-dichlorophenyl)piperazin-1-yl)butan-1-amine (9i)
Compound 9i was prepared as colorless solid from 8c and 4-methoxylbenzoic acid. Yield: 32.3%. Mp: 111-113 °C.
1H NMR (300 MHz, CDCl3) δ 8.04 – 7.85 (m, 2H), 7.36 (d, J = 2.4 Hz, 1H), 7.16 (dd, J = 8.6, 2.4 Hz, 1H), 7.06 –
6.85 (m, 3H), 5.65 (s, 1H), 3.88 (s, 3H), 3.31 (t, J = 6.0 Hz, 2H), 3.12 (t, J = 4.3 Hz, 4H), 2.67 (s, 4H), 2.48 (t, J =
6.7 Hz, 2H), 1.84 – 1.57 (m, 4H). 13C NMR (151 MHz, cdcl3) δ 173.76, 169.14, 162.79, 148.06, 130.23, 129.67,
129.41, 128.09, 127.55, 121.22, 117.16, 114.23, 58.24, 55.44, 53.20, 50.90, 43.34, 27.76, 24.51.
N-(5-(3-Methoxylphenyl)-1,2,4-oxadiazol-3-yl)-4-(4-(2,4-dichlorophenyl)piperazin-1-yl)butan-1-amine (9j)
1
Compound 9j was prepared as colorless liquid from 8c and 3-methoxylbenzoic acid. Yield: 47.2%. H NMR (300
MHz, CDCl3) δ 7.62 (d, J = 7.7 Hz, 1H), 7.53 (s, 1H), 7.38 (dd, J = 10.9, 5.2 Hz, 2H), 7.13 (ddd, J = 21.6, 8.4, 2.4
Hz, 2H), 7.00 (d, J = 8.6 Hz, 1H), 5.81 (s, 1H), 3.85 (s, 3H), 3.32 (s, 2H), 3.12 (s, 4H), 2.67 (s, 4H), 2.48 (t, J = 6.6
Hz, 2H), 1.87 – 1.55 (m, 4H). 13C NMR (151 MHz, cdcl3) δ 173.76, 169.17, 159.71, 148.04, 130.19, 129.99, 129.38,
128.09, 127.59, 125.67, 121.21, 120.21, 118.59, 112.45, 77.20, 76.99, 76.78, 58.28, 55.39, 53.21, 50.91, 43.35,
27.78, 24.54.