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Can. J. Chem. Vol. 85, 2007
4H). EI-MS m/z (%): 235 (28, M+), 136 (100), 121 (57), 77
(23), 65 (15), 51 (12).
(m, 2H), 2.08–2.20 (m, 2H), 2.90 (br s, NH), 3.10 (ddd, J =
4.2, 9.5, 11.0 Hz, 1H), 3.30 (ddd, J = 4.0, 10.0, 10.0 Hz,
1H), 6.68–6.78 (m, 3H), 7.10–7.20 (m, 2H). EI-MS m/z (%):
227 (30, M+), 191 (25), 167 (51), 114 (19), 96 (21), 77
(100), 56 (31), 52 (37), 45 (23).
1-Chloro-3-(3-chloro-2-methylphenyl)aminopropan-2-ol
(3h)
Brown coloured syrup. IR (neat) ν: 3403, 3386, 3072,
2941, 2837, 1605, 1518, 1461, 1404, 1346, 1286, 1231,
1203, 1172, 1134, 1108, 1031, 917, 846, 748 cm–1. 1H NMR
(200 MHz, CDCl3) δ: 2.28 (s, 3H), 2.45 (br s, 1H), 3.25 (q,
J = 6.5 Hz, 1H), 3.42 (dd, J = 4.0, 9.5 Hz, 1H), 3.65–3.75
(m, 2H), 4.00 (br s, 1H), 4.15 (br s, 1H), 6.53 (d, J = 7.0 Hz,
1H), 6.80 (d, J = 7.0 Hz, 1H), 7.05 (t, J = 7.0 Hz, 1H). EI-
MS m/z (%): 234 (10, M+), 232 (15), 156 (41), 154 (100),
125 (15), 117 (10), 89 (20), 77 (12), 51 (10), 43 (12).
1-trans-2-(4-Nitrophenylamino)cyclohexanol (3n)
Brown solid; mp 71–72 °C. IR (KBr) ν: 3394, 2928,
2856, 1740, 1622, 1582, 1528, 1453, 1347, 1262, 1133,
1
1067, 949, 854, 815, 792, 735 cm–1. H NMR (200 MHz,
CDCl3) δ: 0.80–0.95 (m, 1H), 1.22–1.45 (m, 3H), 1.70–1.85
(m, 2H), 2.08–2.20 (m, 2H), 3.20 (ddd, J = 4.2, 9.5,
11.0 Hz, 1H), 3.40 (ddd, J = 4.0, 10.0, 11.0 Hz, 1H), 3.80
(br s, 1H), 6.95 (d, J = 7.5 Hz, 1H), 7.30 (t, J = 7.5 Hz, 1H),
7.55 (t, J = 7.5 Hz, 1H). EI-MS m/z (%): 237 (79, M+),
221(26), 194 (10), 178 (96), 152 (32), 139 (15), 121 (18),
118 (40), 106 (14), 92 (51), 65 (63), 57 (66), 41 (100).
1-Phenoxy-3-phenylaminopropan-2-ol (3i)
Colourless oil. IR (neat) ν: 3408, 3391, 3056, 2926, 2872,
1602, 1562, 1517, 1491, 1362, 1243, 1123, 1039, 947, 861,
1
742 cm–1. H NMR (200 MHz, CDCl3) δ: 3.15 (dd, J = 7.5,
1-trans-2-(2-Methoxyphenylamino)cyclohexanol (3o)
White solid; mp 56–57 °C. IR (KBr) ν: 3380, 3063, 3000,
2933, 2858, 1601, 1511, 1457, 1431, 1401, 1343, 1302,
1224, 1177, 1141, 1118, 1068, 1030, 936, 903, 850, 804,
12.0 Hz, 1H), 3.36 (dd, J = 4.5, 12.0 Hz, 1H), 3.50–3.60 (m,
2H), 4.02–4.35 (m, 1H), 6.55–6.70 (m, 3H), 7.15–7.35 (m,
7H). EI-MS m/z (%):243 (18, M+), 150 (23), 137 (32), 106
(100), 93 (14), 77 (41), 75 (16), 51 (31).
1
799, 738 cm–1. H NMR (200 MHz, CDCl3) δ: 0.98–1.18
(m, 1H), 1.25–1.41 (m, 3H), 1.70–1.80 (m, 2H), 2.05–2.20
(m, 2H), 2.75 (br s, NH), 3.10 (ddd, J = 4.1, 9.2, 11.0 Hz,
1H), 3.40 (ddd, J = 4.1, 9.2, 11.0 Hz, 1H), 3.85 (s, 3H),
6.60–6.85 (m, 4H). EI-MS m/z (%): 221 (90, M+), 164 (12),
162 (100), 150 (15), 136 (26), 123 (90), 108 (84), 106 (11),
80 (81), 65 (11), 53 (31).
3-(2,4-Dichlorophenyl)-1-(phenoxy)aminopropan-2-ol (3j)
Colourless oil. IR (neat) ν: 3397, 3061, 3047, 2961, 2851,
1631, 1604, 1501, 1487, 1432, 1342, 1213, 1143, 1019, 951,
1
841, 748 cm–1. H NMR (200 MHz, CDCl3) δ: 3.18 (dd, J =
6.0, 11.0 Hz, 1H), 3.32 (dd, J = 4.0, 11.0 Hz, 1H), 3.52–3.63
(m, 2H), 4.05–4.30 (m, 1H), 6.65 (d, J = 7.0 Hz, 1H), 7.10
(d, J = 7.0 Hz, 1H), 7.30 (s, 1H). EI-MS m/z (%): 312 (18,
M+), 275 (10), 219 (23), 175 (18), 163 (12), 146 (31), 134
(21), 109 (100), 90 (24), 74 (36), 49 (21).
1-trans-2-(2-Chloro-3-methylphenylamino)cyclohexanol
(3p)
Light coloured solid; mp 49–50 °C. IR (KBr) ν: 3408,
3374, 3061, 2935, 2861, 1603, 1585, 1506, 1456, 1429,
1389, 1346, 1312, 1267, 1214, 1163, 1131, 1097, 1059, 946,
3-(4-Nitrophenyl)-1-(propargyloxy)aminopropan-2-ol (3k)
Colourless solid; mp 73–75 °C. IR (KBr) ν: 3409, 3378,
3063, 2951, 2841, 1605, 1509, 1432, 1361, 1302, 1278,
1141, 1109, 1023, 972, 873, 804, 753 cm–1. 1H NMR
(200 MHz, CDCl3) δ: 3.12 (dd, J = 5.0, 10.5 Hz, 1H), 3.30
(dd, J = 5.0, 10.5 Hz, 1H), 3.50–3.60 (m, 2H), 3.88 (s, 3H),
3.93–3.98 (m, 1H), 6.32 (d, J = 7.0 Hz, 1H), 6.50–6.60 (m,
2H), 6.75 (d, J = 7.0 Hz, 1H), 7.30–7.45 (m, 5H). EI-MS
m/z (%): 250 (22, M+), 242 (10), 180 (26), 136 (31), 107
(100), 93 (19), 76 (48), 51(21).
1
913, 854, 763, 748 cm–1. H NMR (200 MHz, CDCl3) δ:
0.94–1.15 (m, 1H), 1.23–1.40 (m, 3H), 1.68–1.79 (m, 2H),
2.02–2.20 (m, 2H), 2.40 (s, 3H), 2.85 (br s, NH), 3.15 (ddd,
J = 4.3, 9.6, 11.0 Hz, 1H), 3.38 (ddd, J = 4.3, 9.6, 11.0 Hz,
1H), 6.50 (d, J = 6.5 Hz, 1H), 6.75 (d, J = 6.5 Hz, 1H), 7.05
(t, J = 6.5 Hz, 1H). EI-MS m/z (%): 241 (30, M+), 204 (12),
189 (10), 127 (100), 114 (56), 90 (39), 75 (31), 65 (11), 51
(32).
3-(3-Chloro-2-methylphenyl)-1-(phenoxy)aminopropan-2-
ol (3l)
References
1. (a) T. Kino, H. Halanaka, M. Hashimoto, M. Nishiyama, T.
Goto, M. Okuhara, M. Kohsaka, H. Aoki, and H. Imanaka. J.
Antibiot. 40, 1249 (1987); (b) D.S. Bose and A.V. Narsaiah.
Bioorg Med. Chem. 3, 627 (2005); (c) E.J. Corey and X-M.
Cheng. The logic of chemical synthesis. John Wiley, New
York. 1989; (d) P.W. Erhardt, C.M. Woo, W.G. Anderson, and
R.J. Gorczynski. J. Med. Chem. 25, 1408 (1982); ( f ) A.V.
Narsaiah. Synth. Commun. 1897 (2006).
2. (a) M. Curini, F. Epifano, M.C. Marcotullio, and O. Rosati.
Eur. J. Org. Chem. 4149 (2001); (b) L.D. Pachon, P. Gamez,
J.J.M. Van Bessel, and J. Reedijk. Tetrahedron Lett. 44, 6025
(2003); (c) M.M. Khodaei, A.R. Khosropour, and K. Ghozati.
Tetrahedron Lett. 45, 3525 (2004); (d) T. Ollevier and G.
Lavie- Compin. Tetrahedron Lett. 45, 49 (2004); (e) Y.
Yamamoto, N. Asao, M. Meguro, N. Tsukade, H. Nemoto, N.
Adayari, J.G. Wilson, and H. Nakamura. J. Chem. Soc., Chem.
Light yellow oil. IR (neat) ν: 3403, 3371, 3065, 2943,
2849, 1636, 1606, 1541, 1508, 1431, 1362, 1308, 1256,
1
1137, 1046, 1012, 937, 851, 749 cm–1. H NMR (200 MHz,
CDCl3) δ: 2.37 (s, 3H), 3.18 (dd, J = 5.5, 10.5 Hz, 1H), 3.32
(dd, J = 5.5, 10.5 Hz, 1H), 3.45–3.58 (m, 2H), 3.90–3.97 (m,
1H), 6.20 (d, J = 7.0 Hz, 1H), 6.70–6.85 (m, 1H), 7.30–7.40
(m, 6H). EI-MS m/z (%): 291 (21, M+), 256 (18), 154 (21),
137 (100), 119 (56), 104 (11), 93 (15), 77 (25), 61 (412),
57(37), 43 (51).
1-trans-2-(4-Chlorophenylamino)cyclohexanol (3m)
White solid; mp. 61–62 °C. IR (KBr) ν: 3394, 3276,
3081, 2961, 2846, 1739, 1608, 1526, 1452, 1381, 1232,
1112, 1073, 952, 847, 753 cm–1. 1H NMR (200 MHz,
CDCl3) δ: 0.98–1.08 (m, 1H), 1.28–1.41 (m, 3H), 1.70–1.85
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