28
H. Mofakham et al. / Journal of Molecular Catalysis A: Chemical 360 (2012) 26–34
148.2, 170.7. Anal. Calcd for C22H21N3O5S: C, 60.12; H, 4.82; N, 9.56;
found C, 60.12; H, 4.82; N, 9.56.
2.4.12. 2-(2-Hydroxy-5-methylphenylamino)-2-(4-
chlorophenyl)-N-cyclohexylacetamide
(6b)
Brown powder; mp 203–204 ◦C. IR (KBr) cm−1: 3394, 3349,
3188, 3033, 2930, 2856, 1656, 1602, 1524, 1408, 1356, 1306. 1H
NMR (300.13 MHz, DMSO-d6) ı: 1.00–1.80 (10H, m, 5CH2 of cyclo-
hexyl), 2.02 (3H, s, CH3), 3.48 (1H, m, CH of cyclohexyl), 5.02 (1H,
ABq, J = 7.6, CH), 5.27 (1H, ABq, J = 7.7, NH), 6.06 (1H, s, CH-Ar), 6.21
(1H, d, J3 = 7.8, CH-Ar), 6.56 (1H, d, J3 = 7.8, CH-Ar), 7.38 (2H, ABq,
J = 8.4, CH-Ar), 7.46 (2H, ABq, J = 7.1, CH-Ar), 8.24 (1H, d, J3 = 7.48,
NH), 9.26 (1H, OH). 13C NMR (75.47 MHz, DMSO-d6) ı: 21.3, 24.7,
24.8, 25.6, 32.4, 32.7, 48.0, 59.4, 112.1, 114.0, 117.4, 128.2, 128.8,
132.4, 135.2, 139.5, 142.6, 169.7. Anal. Calcd for C21H25ClN2O2: C,
67.64; H, 6.76; N, 7.51; found C, 67.62; H, 6.70; N, 7.41.
2.4.7. 1-(Phenylamino)-N-(tosylmethyl)cyclohexanecarboxamide
(5g)
Brown powder; mp 187 ◦C. IR (KBr) cm−1: 3370, 3051, 3007,
2936, 2857, 1672, 1600, 1496, 1388, 1316. 1H NMR (300.13 MHz,
DMSO-d6) ı: 1.20–1.90 (10H, m, 5CH2 of cyclohexyl), 2.44 (3H, s,
CH3), 4.68 (2H, s, CH2), 6.65 (3H, m, CH-Ar), 6.90 (1H, s, NH), 7.18
(1H, d, J3 = 7.0, CH-Ar), 7.31 (1H, ABq, J3 = 7.5, CH-Ar), 7.73 (1H, ABq,
J3 = 7.6, CH-Ar), 7.92 (1H, s, NH). 13C NMR (75.47 MHz, DMSO-d6) ı:
21.1, 21.7, 24.8, 31.0, 60.3, 112.8, 113.6, 115.4, 128.8, 129.2, 129.8,
134.2, 145.3, 171.5. Anal. Calcd for C21H26N2O3S: C, 65.26; H, 6.78;
N, 7.25; found C, 65.16; H, 6.71; N, 7.20.
2.4.13. 2-(2-Hydroxyphenylamino)-N-cyclohexyl-2-(4-
methoxyphenyl)acetamide
(6c)
2.4.8.
2-(Benzylamino)-2-(4-fluorophenyl)-N-(tosylmethyl)acetamide
(5h)
Black powder; mp 180–182 ◦C. IR (KBr) cm−1: 3369, 3350,
3166, 2931, 2850, 1653, 1600, 1518, 1440, 1374, 1310. 1H NMR
(300.13 MHz, DMSO-d6) ı: 1.00–1.80 (10H, m, 5CH2 of cyclohexyl),
3.47 (1H, m, CH of cyclohexyl), 3.70 (3H, s, CH3), 4.91 (1H, d, J = 7.5,
CH), 5.26 (1H, d, J = 7.5, NH), 6.24 (1H, d, J3 = 7.4, CH-Ar), 6.39 (1H,
dd, J3 = 7.2, 7.2, CH-Ar), 6.52 (1H, dd, J3 = 7.3, 7.3, CH-Ar), 6.66 (2H, d,
J3 = 7.4, CH-Ar), 6.86 (2H, d, J3 = 8.0, CH-Ar), 7.35 (2H, d, J3 = 8.0, CH-
Ar), 8.13 (1H, d, J3 = 7.6, NH), 9.44 (1H, OH). 13C NMR (75.47 MHz,
DMSO-d6) ı: 24.8, 24.9, 25.6, 32.5, 32.8, 48.0, 55.4, 59.5, 111.2,
114.0, 114.2, 116.9, 119.9, 128.2, 132.2, 135.7, 144.7, 159.0, 170.4.
Anal. Calcd for C21H26N2O3: C, 71.16; H, 7.39; N, 7.90; found C,
71.16; H, 7.30; N, 7.85.
Brown powder; mp 120–121 ◦C. IR (KBr) cm−1: 3330, 3058,
2935, 2855, 1679, 1613, 1530, 1434, 1358, 1318. 1H NMR
(300.13 MHz, DMSO-d6) ı: 2.36 (3H, s, CH3), 3.39 (2H, s, CH2),
4.50–4.70 (3H, m, CH2 and CH), 5.58 (1H, s, NH), 7.00–8,00 (14H,
CH-Ar and NH). 13C NMR (75.47 MHz, DMSO-d6) ı: 21.2, 50.7, 61.0,
61.5, 115.5, 125.9, 128.1, 128.3, 128.5, 128.8, 128.9, 129.0, 129.3,
129.4, 129.5, 130.0, 130.1, 130.2, 130.6, 138.3, 145.3, 145.7, 171.0.
Anal. Calcd for C23H23FN2O3S: C, 64.77; H, 5.44; F, 4.45; N, 6.57;
found C, 64.70; H, 5.41; F, 4.45; N, 6.55.
2.4.9.
2.4.14. 2-(2-Hydroxy-5-methylphenylamino)-N-cyclohexyl-2-(4-
methoxyphenyl)acetamide
(6d)
2-(Benzylamino)-2-(2-bromophenyl)-N-(tosylmethyl)acetamide
(5i)
Cream powder; mp 180–181 ◦C. IR (KBr) cm−1: 3360, 3334,
3168, 2932, 2850, 1678, 1590, 1528, 1445, 1355, 1302. 1H NMR
(300.13 MHz, DMSO-d6) ı: 2.27 (3H, s, CH3), 4.50–4.70 (5H, m, 2CH2
and CH), 5.60 (1H, s, NH), 6.90–8.00 (14H, CH-Ar and NH). Anal.
Calcd for C23H23BrN2O3S: C, 56.68; H, 4.76; N, 5.75; found C, 56.68;
H, 4.76; Br, 16.39; N, 5.75.
Green powder; mp 175–178 ◦C. IR (KBr) cm−1: 3394, 3349, 3930,
2856, 1651, 1605, 1519, 1451, 1305. 1H NMR (300.13 MHz, DMSO-
d6) ı: 1.00–1.80 (10H, m, 5CH2 of cyclohexyl), 2.00 (3H, s, CH3), 3.44
(1H, m, CH of cyclohexyl), 3.68 (3H, s, CH3), 4.87 (1H, d, J = 5.5, CH),
5.12 (1H, s, NH), 6.06 (1H, s, CH-Ar), 6.17 (1H, d, J3 = 5.0, CH-Ar), 6.49
(1H, s, CH-Ar), 6.52 (2H, ABq, J3 = 5.2, CH-Ar), 6.86 (2H, s, CH-Ar),
8.08 g (1H, s, NH), 9.16 (1H, OH). 13C NMR (75.47 MHz, DMSO-d6)
ı: 21.3, 24.7, 24.8, 25.6, 32.5, 32.8, 47.9, 55.4, 59.5, 112.0, 113.8,
114.2, 117.1, 128.2, 132.3, 135.6, 142.5, 159.0, 170.4. Anal. Calcd
for C22H28N2O3: C, 71.71; H, 7.66; N, 7.60; found C, 71.61; H, 7.60;
N, 7.50.
2.4.10. 2-(Allylamino)-N-tert-butyl-2-phenylacetamide (5j)
Yellow liquid. IR (KBr) cm−1: 3360, 3324, 3160, 2935, 2855,
1676, 1590, 1440, 1365. 1H NMR (300.13 MHz, DMSO-d6) ı: 1.25
(9H, s, CH3), 3.15 (m, 2H, CH2), 5.00 (br, 1H, CH), 5.10 (br, 1H,
CH), 5.75 (1H, s, NH), 6.95–7.60 (6H, CH-Ar and NH). 13C NMR
(75.47 MHz, DMSO-d6) ı: 28.2, 50.1, 50.4, 68.2, 115.7, 125.5, 135.5,
139.2, 167.5. Anal. Calcd for C15H22N2O: C, 73.13; H, 9.00; N, 11.37;
found C, 73.08; H, 9.01; N, 11.27.
2.4.15. 1-(2-Hydroxyphenylamino)-N-
cyclohexylcyclohexanecarboxamide
(6e)
Brown powder; mp 204–206 ◦C. IR (KBr) cm−1: 3391, 3360,
3200, 3046, 2933, 2850, 1641, 1598, 1512, 1447, 1376. 1H NMR
(300.13 MHz, DMSO-d6) ı: 1.00–1.90 (20H, m, 10CH2 of cyclo-
hexyl), 3.54 (1H, m, CH of cyclohexyl), 4.66 (1H, s, NH), 6.27 (1H, d,
J = 6.6, CH-Ar), 6.30–6.60 (2H, m, CH-Ar), 6.73 (1H, d, J = 6.6, CH-Ar),
7.48 (1H, d, J = 7.4, NH), 9.58 (1H, OH). 13C NMR (75.47 MHz, DMSO-
d6) ı: 21.2, 25.1, 25.4, 25.6, 31.4, 32.6, 47.8, 59.3, 114.3, 114.8, 118.0,
119.4, 133.6, 145.8, 175.0. Anal. Calcd for C19H28N2O2: C, 72.12; H,
8.92; N, 8.85; found C, 72.07; H, 8.90; N, 8.75.
2.4.11. 2-(2-Hydroxyphenylamino)-2-(4-chlorophenyl)-N-
cyclohexylacetamide
(6a)
Brown powder; mp 208 ◦C. IR (KBr) cm−1: 3380, 3344, 3171,
3049, 2930, 2854, 1648, 1599, 1520, 1440, 1365, 1306. 1H NMR
(300.13 MHz, DMSO-d6) ı: 1.00–1.80 (10H, m, 5CH2 of cyclohexyl),
3.45 (1H, m, CH of cyclohexyl), 5.03 (1H, ABq, J = 7.8, CH), 5.37 (1H,
ABq, J = 7.9, NH), 6.21 (1H, d, J3 = 6.8, CH-Ar), 6.40 (1H, ddd, J3 = 7.5,
7.5, J4 = 1.3, CH-Ar), 6.51 (1H, ddd, J3 = 7.2, 7.5, J4 = 1.1, CH-Ar), 6.69
(1H, dd, J3 = 7.6, J4 = 1.2, CH-Ar), 7.37 (2H, ABq, J = 8.5, CH-Ar), 7.46
2.4.16. 1-(2-Hydroxyphenylamino)-N-
cyclohexylcyclopentanecarboxamide
(6f)
(2H, ABq, J = 8.5, CH-Ar), 8.27 (1H, d, J = 7.8, NH), 9.53 (1H, OH). 13
C
Yellow powder; mp 219 ◦C. IR (KBr) cm−1: 3393, 3065, 2947,
2853, 1675, 1604, 1558, 1515, 1449, 1376, 1331. 1H NMR
(300.13 MHz, DMSO-d6) ı: 1.00–2.40 (18H, m, 9CH2 of cyclohexyl
and cyclopentyl), 3.54 (1H, m, CH of cyclohexyl), 4.88 (1H, s, NH),
NMR (75.47 MHz, DMSO-d6) ı: 24.7, 24.8, 25.6, 32.4, 32.7, 48.1,
59.3, 111.3, 114.1, 117.2, 119.9, 128.8, 128.9, 132.4, 135.3, 139.5,
144.8, 169.7. Anal. Calcd for C20H23ClN2O2: C, 66.94; H, 6.46; N,
7.81; found C, 66.94; H, 6.46; N, 7.81.