Med Chem Res
7.70 (td, J = 7.6, 1.6 Hz, 1H, H-7), 7.33 (d, J = 7.8 Hz, 1H,
H-6), 7.18 (dd, J = 7.1, 5.2 Hz, 1H, H-8), 6.75 (d, J = 9.1
Hz, 2H, H-11, H-15), 6.58 (t, J = 6.4 Hz, 2H, H-12, H-14),
4.64 (dd, J = 14.9, 2.2 Hz, 2H, H-4), 4.28–4.23 (m, 1H, H-
2), 3.89 (dd, J = 14.9, 2.2 Hz, 1H, H-3), 3.79–3.72 (m, 1H,
H-18), 3.70 (s, 3H, H-16), 3.52 (ddd, J = 14.9, 9.6, 5.3 Hz,
2H, H-1), 3.44 (s, 4H, H-17, H-19), 3.41–3.36 (m, 1H, H-
3); 13C NMR (125 MHz, CDCl3): δ 159.7 (C-5), 151.5 (C-
13), 149.1 (C-9), 142.1 (C-10), 137.3 (C-7), 122.4 (C-8),
122.2 (C-6), 114.9 (C-11, C-15), 113.2 (C-12, C-14), 74.9
(C-1), 68.0 (C-2), 59.4 (C-17, C-19), 58.9 (C-4), 58.4 (C-3),
55.8 (C-16, C-18); HRMS (EI+) calculated for
C19H26N3O2: 328.2025, found 328.2038.
2H, H-3), 3.48–3.38 (m, 5H, H-15, H-16, H-17, H-18),
2.90–2.85 (m, 1H, H-15, H-18), 2.66–2.58 (m, 2H, H-1),
2.56–2.29 (m, 2H, H-15, H-18); 13C NMR (50 MHz,
CDCl3): δ 146.8 (C-5), 141.9 (C-12), 129.0 (C-11, C-13),
126.8 (C-8), 125.0 (C-7), 124.3 (C-6), 122.3 (C-9), 114.6
(C-10, C-14), 74.3 (C-2), 68.5 (C-1), 66.9 (C-16, C-17),
65.5 (C-3), 62.4 (C-4), 59.2 (C-15, C-18), 54.0 (C-15, C-
18); HRMS (EI+) calculated for C20H19N2O2: 367.1247,
found 367.1243.
1-(Azetidin-1-yl)-3-((4-chlorophenyl)(thien-2-ylmethyl)
amino)propan-2-ol (8k) Yield: 96%; amber oil; IR (KBr)
νmax (cm−1): 3434, 2891, 1597, 1500, 1366, 1219, 1125,
1
1101, 810, 701; H NMR (300 MHz, CDCl3): δ 7.18–6.95
1-((4-Methoxyphenyl)(pyridin-2-ylmethyl)amino)-3-(piper-
azin-1-yl)propan-2-ol (8h) Yield: 85%; amber oil; IR
(KBr) νmax (cm−1): 3390, 2932, 1659, 1594, 1514, 1436,
1244, 1181, 1039, 817, 760; 1H NMR (300 MHz, CDCl3): δ
7.15–7.11 (m, 3H, H-8, H-11, H-13), 6.90 (dd, J = 9.2, 4.2
Hz, 2H, H-6, H-7), 6.74 (dd, J = 9.1, 2.2 Hz, 2H, H-10, H-
14), 4.72 (d, J = 9.1 Hz, 2H, H-4), 4.10–3.97 (s, 1H, H-2),
3.52–3.33 (m, 5H, H-3, H-15, H-18), 3.01–2.85 (m, 3H, H-
16, H-17), 2.61–2.24 (m, 4H, H-1, H-3, H-16, H-17), 1.30
(s, 1H, NH); 13C NMR (125 MHz, CDCl3): δ 159.0 (C-13),
148.5 (C-9), 136.6 (C-7), 122.4 (C-5), 122.3 (C-6), 122.2
(C-10), 120.4 (C-8), 114.8 (C-11, C-15), 113.2 (C-12, C-
14), 74.8 (C-2), 68.0 (C-1), 64.1 (C-3, C-17, C-20), 59.4 (C-
4), 55.7 (C-18, C-19); HRMS (EI+) calculated for
C18H25ClN3OS: 366.1407, found 366.1375.
(m, 3H, H-8, H-11, H-13), 6.92–6.88 (m, 2H, H-6, H-7),
6.86–6.74 (d, J = 6.8 Hz, 2H, H-10, H-14), 4.71 (s, 2H, H-
4), 4.10–4.01 (s, 1H, H-4), 3.51–3.32 (m, 8H, H-1, H-3, H-
15, H-16, H-17), 2.43 (s, 1H, H-1), 1.26–0.87 (s, 1H, H-3);
13C NMR (50 MHz, CDCl3): δ 146.8 (C-5), 141.7 (C-12),
129.0 (C-11, C-13), 126.9 (C-8), 125.1 (C-7), 124.4 (C-6),
122.4 (C-9), 114.7 (C-10, C-14), 74.3 (C-1), 68.6 (C-2),
59.2 (C-15, C-17), 54.0 (C-4), 51.1 (C-3, C-16); HRMS
(EI+) calculated for C17H22ClN2OS: 337.1141, found
337.2051.
1-((4-Chlorophenyl)(thien-2-ylmethyl)amino)-3-(piperazin-
1-yl)propan-2-ol (8l) Yield: 85%; amber oil; IR (KBr)
νmax (cm−1): 3400, 2936, 2882, 2820, 1596, 1499, 1366,
1219, 1127, 1101, 809, 700; 1H NMR (300 MHz, CDCl3): δ
7.15–7.11 (m, 3H, H-8, H-11, H-13), 6.90 (dd, J = 9.2, 4.2
Hz, 2H, H-6, H-7), 6.74 (dd, J = 9.1, 2.2 Hz, 2H, H-10, H-
14), 4.72 (d, J = 9.1 Hz, 2H, H-4), 4.10–3.97 (s, 1H, H-2),
3.52–3.33 (m, 5H, H-3, H-15, H-18), 3.01–2.85 (m, 3H, H-
16, H-17), 2.61–2.24 (m, 4H, H-1, H-3, H-16, H-17), 1.30
(s, 1H, NH); 13C NMR (75 MHz, CDCl3): δ 146.9 (C-5),
142.0 (C-12), 128.9 (C-11, C-13), 126.8 (C-8), 125.2 (C-7),
124.4 (C-6), 122.1 (C-9), 114.8 (C-10, C-14), 74.1 (C-2),
68.6 (C-1), 59.1 (C-3, C-15, C-18), 54.2 (C-4), 51.1 (C-16,
C-17); HRMS (EI+) calculated for C18H25ClN3OS:
366.1407, found 366.1375.
1-((4-Methoxyphenyl)(thien-2-ylmethyl)amino)-3-morpho-
linopropan-2-ol (8i) Yield: 85%; amber oil; IR (KBr) νmax
(cm−1): 3430, 2932, 2830, 1635, 1512, 1455, 1242, 1116,
1
1036; H NMR (200 MHz, CDCl3,): δ 7.19–7.13 (m, 1H,
H-8), 6.93–6.75 (m, 6H, H-6, H-7, H-10, H-11, H-13, H-
14), 4.65 (s, 2H, H-4), 4.03–3.89 (m, 1H, H-2), 3.78–3.65
(m, 7H, H-15, H-17, H-18), 3.35–3.25 (m, 2H, H-3), 3.13
(s, 1H, OH), 2.68–2.52 (m, 2H, H-16, H-19), 2.49–2.36 (m,
4H, H-1, H-16, H-19); 13C NMR (50 MHz, CDCl3): δ 153.0
(C-5), 143.1 (C-12), 142.5 (C-9), 126.7 (C-8), 125.2 (C-7),
124.5 (C-6), 117.2 (C-11, C-13), 114.7 (C-10, C-14), 67.1
(C-17, C-18), 65.5 (C-2), 62.7 (C-1), 56.4 (C-3), 55.7 (C-
15), 53.9 (C-16, C-19), 52.8 (C-4); HRMS (EI+) calculated
for C19H26N2O3S: 362.1664, found 362.1678.
1-((Furan-2-ylmethyl)(4-methoxyphenyl)amino)-3-morpho-
linopropan-2-ol (8m) Yield: 92%; dark orange oil; IR
(KBr) νmax (cm−1): 3434, 2927, 2854, 1513, 1243, 1116,
1
1037; H NMR (300 MHz, CDCl3): δ 7.34 (s, 1H, H-9),
1-((4-Chlorophenyl)(thien-2-ylmethyl)amino)-3-morpholi-
nopropan-2-ol (8j) Yield: 78%; amber oil; IR (KBr) νmax
(cm−1): 3429, 2926, 2891, 2821, 1596, 1501, 1454, 1417,
1366, 1326, 1221, 1192, 1116, 1007, 909, 510, 731, 702;
1H NMR (200 MHz, CDCl3): δ 7.15 (dd, J = 7.0, 4.5 Hz,
3H, H-8, H-10, H-14), 6.91 (dd, J = 8.9, 4.0 Hz, 2H, H-6,
H-7), 6.75 (dd, J = 9.1, 2.3 Hz, 2H, H-11, H-13), 4.73 (d, J
= 8.8 Hz, 2H, H-4), 4.13–3.95 (s, 1H, H-2), 3.72–3.63 (m,
6.87–6.78 (m, 4H, H-10, H-11, H-13, H-14), 6.27 (s, 1H, H-
7), 6.11 (s, 1H, H-6), 4.43 (s, 2H, H-4), 3.98–3.91 (m, 1H,
H-2), 3.75–3.68 (m, 7H, H-15, H-17, H-18), 3.35–3.25 (m,
2H, H-3), 2.60–2.56 (m, 2H, H-16, H-19), 2.43–2.31 (m,
4H, H-1, H-16, H-19); 13C NMR (75 MHz, CDCl3): δ 152.5
(C-12), 143.3 (C-5), 141.7 (C-8, C-9), 116.7 (C-10, C-14),
114.5 (C-11, C-13), 110.1 (C-7), 107.6 (C-6), 66.8 (C-17,
C-18), 65.4 (C-2), 62.5 (C-1), 56.4 (C-3), 55.6 (C-15), 53.9