1146
E. Vessally et al.
25.49, 32.71, 32.76, 48.42, 75.34, 121.95, 128.22, 129.04,
129.85, 133.25, 133.63, 136.59, 148.98, 155.20, 165.18,
165.90 ppm.
a-Benzoyloxy-N-cyclohexylpyridine-4-acetamide
(4k, C20H22N2O3)
White powder, yield 95%; m.p.: 155–157 °C; IR (KBr):
ꢀm = 3,287 (NH), 3,087, 2,931, 1,735 (C=O of ester), 1,658
a-(4-Chlorobenzoyloxy)-N-cyclohexylpyridine-3-acetamide
(4g, C20H21ClN2O3)
(C=O of amide), 1,559, 1,265, 1,118 (C–O) cm-1 1H
;
NMR (CDCl3): d = 0.86–2.32 (m, 10H, 5 CH2 of cyclo-
hexyl), 3.76–3.79 (m, 1H, N–CH), 6.29 (s, 1H, CH–O),
6.78–6.81 (d, J = 7.24 Hz, 1H, NH), 7.24–8.58 (m, 9H,
arom CH) ppm; 13C NMR (CDCl3): d = 24.59, 24.67,
25.49, 32.73, 32.76, 48.42, 77.56, 121.95, 128.12, 129.15,
129.90, 132.93, 149.02, 155.20, 165.18, 165.90 ppm.
White powder, yield 96%; m.p.: 213–215 °C; IR (KBr):
ꢀ
m = 3,279 (NH), 3,099, 2,963, 1,732 (C=O of ester), 1,667
(C=O of amide), 1,560, 1,447, 1,261, 1,112 (C–O), 1,103
(C–Cl) cm-1; H NMR (CDCl3): d = 1.04–2.26 (m, 10H,
1
5 CH2 of cyclohexyl), 3.26–3.30 (m, 1H, N–CH), 5.77
(s, 1H, CH–O), 6.10 (s, 1H, NH), 7.44–8.77 (m, 8H, arom
CH) ppm; 13C NMR (CDCl3): d = 24.55, 24.62, 25.43,
32.69, 32.73, 48.74, 75.35, 121.95, 128.25, 128.29, 131.14,
133.15, 134.59, 138.63, 149.38, 153.20, 165.18,
167.73 ppm.
a-(4-Chlorobenzoyloxy)-N-cyclohexylpyridine-4-acetamide
(4l, C20H21ClN2O3)
White powder, yield 96%; m.p.: 213–215 °C; IR (KBr):
ꢀ
m = 3,277 (NH), 3,095, 2,963, 2,928, 1,732 (C=O of ester),
1,660 (C=O of amide), 1,562, 1,261, 1,093 (C–O), 1,029
(C–Cl) cm-1; 1H NMR (CDCl3): d = 0.82–2.37 (m, 10H, 5
CH2 of cyclohexyl), 3.21–3.26 (m, 1H, N–CH), 5.30 (s, 1H,
CH–O), 6.75–6.78 (d, J = 7.24 Hz, 1H, NH), 7.22–8.08 (m,
8H, arom CH) ppm; 13C NMR (CDCl3): d = 24.59, 24.68,
25.65, 32.69, 32.75, 48.49, 77.69, 122.40, 128.32, 128.50,
131.44, 138.82, 149.23, 150.59, 165.50, 166.50 ppm.
N-Cyclohexyl-a-(4-methylbenzoyloxy)pyridine-3-
acetamide (4h, C21H24N2O3)
White powder, yield 96%; m.p.: 217 °C; IR (KBr):
ꢀ
m = 3,283 (NH), 3,087, 2,986, 1,736 (C=O of ester),
1,661 (C=O of amide), 1,559, 1,414, 1,262, 1,094 cm-1
;
1H NMR (CDCl3): d = 1.04–1.75 (m, 10H, 5 CH2 of
cyclohexyl), 2.07 (s, 3H, CH3), 3.35 (m, 1H, N–CH), 5.80
(s, 1H, CH–O), 6.08 (s, 1H, NH), 7.20–8.35 (m, 8H, arom
CH) ppm; 13C NMR (CDCl3): d = 21.42, 24.56, 24.66,
25.50, 32.70, 32.76, 47.85, 75.24, 123.58, 126.80, 127.75,
128.93, 133.29, 136.39, 137.84, 149.68, 155.30, 165.18,
166.91 ppm.
N-Cyclohexyl-a-(4-methylbenzoyloxy)pyridine-4-
acetamide (4m, C21H24N2O3)
White powder, yield 96%; m.p.: 216–218 °C; IR (KBr):
ꢀ
m = 3,281 (NH), 3,086, 2,962, 1,734 (C=O of ester), 1,660
(C=O of amide), 1,559, 1,260, 1,091 (C–O) cm-1 1H
;
NMR (CDCl3): d = 1.11–2.08 (m, 10H, 5 CH2 of cyclo-
hexyl), 2.39 (s, 3H, CH3), 3.30–3.35 (m, 1H, N–CH), 5.75
(s, 1H, CH–O), 6.06 (s, 1H, NH), 7.35–8.62 (m, 8H, arom
CH) ppm; 13C NMR (CDCl3): d = 20.56, 24.58, 24.64,
25.60, 32.70, 32.78, 48.49, 77.56, 121.40, 127.21, 127.80,
128.35, 141.84, 149.23, 155.15, 163.50, 164.46 ppm.
N-Cyclohexyl-a-(4-nitrobenzoyloxy)pyridine-3-acetamide
(4i, C20H21N3O5)
White powder, yield 99%; m.p.: 247–249 °C; IR (KBr):
ꢀ
m = 3,313 (NH), 3,073, 2,936, 1,733 (C=O of ester), 1,656
(C=O of amide), 1,540, 1,260 (NO2), 1,099, 1,037
(C–O) cm-1; H NMR (CDCl3): d = 1.08–2.49 (m, 10H,
1
5 CH2 of cyclohexyl), 3.24–3.36 (m, 1H, N–CH), 5.75
(s, 1H, CH–O), 6.15 (s, 1H, NH), 7.97–8.79 (m, 8H, arom
CH) ppm; 13C NMR (CDCl3): d = 24.50, 24.61, 25.42,
32.76, 32.82, 48.49, 75.52, 121.33, 122.77, 131.36, 133.55,
134.06, 136.79, 148.48, 152.09, 153.59, 163.64,
165.24 ppm.
N-Cyclohexyl-a-(4-nitrobenzoyloxy)pyridine-4-acetamide
(4n, C20H21N3O5)
White powder, yield 99%; m.p.: 242–243 °C; IR (KBr):
ꢀ
m = 3,313 (NH), 3,073, 2,936, 1,733 (C=O of ester), 1,656
(C=O of amide), 1,540, 1,260 (N=O), 1,099, 1,037
(C–O) cm-1; H NMR (CDCl3): d = 1.03–2.06 (m, 10H,
1
5 CH2 of cyclohexyl), 3.35–3.47 (m, 1H, N–CH), 5.84 (s,
1H, CH–O), 6.25 (s, 1H, NH), 7.24–8.60 (m, 8H, arom
CH) ppm; 13C NMR (CDCl3): d = 24.50, 24.58, 25.00,
32.68, 32.72, 48.59, 77.42, 120.97, 121.33, 131.00, 134.06,
149.23, 152.09, 154.20, 163.54, 165.14 ppm.
N-Cyclohexyl-a-(4-methoxybenzoyloxy)pyridine-3-
acetamide (4j, C21H24N2O4)
White powder, yield 96%; m.p.: 231–232 °C; IR (KBr):
ꢀ
m = 3,297 (NH), 3,089, 2,929, 1,734 (C=O of ester), 1,658
(C=O of amide), 1,559, 1,448, 1,265, 1,117 (C–O) cm-1
;
1H NMR (CDCl3): d = 1.11–2.10 (m, 10H, 5 CH2 of
cyclohexyl), 3.76–3.80 (m, 1H, N–CH), 3.87 (s, 3H,
O–CH3), 6.31 (s, 1H, CH–O), 6.72–6.75 (d, J = 7.24 Hz,
1H, NH), 6.93–8.50 (m, 8H, arom CH) ppm; 13C NMR
(CDCl3): d = 24.58, 24.63, 25.70, 32.70, 32.78, 48.36,
55.47, 77.41, 113.78, 121.28, 122.97, 131.98, 133.35,
136.69, 148.62, 153.19, 163.71, 164.84, 166.32 ppm.
N-Cyclohexyl-a-(4-methoxybenzoyloxy)pyridine-4-
acetamide (4o, C21H24N2O4)
White powder, yield 96%; m.p.: 236–237 °C; IR (KBr):
ꢀ
m = 3,289 (NH), 3,095, 2,963, 1,733 (C=O of ester), 1,663
(C=O of amide), 1,561, 1,447, 1,262, 1,123 (C–O) cm-1
;
1H NMR (CDCl3): d = 1.11–2.10 (m, 10H, 5 CH2 of
cyclohexyl), 3.76–3.80 (m, 1H, N–CH), 3.87 (s, 3H,
123