840
N. Shakya et al. / Bioorg. Med. Chem. 17 (2009) 830–847
NMR (CDCl3, 200 MHz): d 1.95–2.04 (m, 2H), 2.74–2.80 (m, 8H),
3.28 (t, J = 5.32 Hz, 2H), 3.82 (bs, 2H), 3.99 (bs, 1H), 4.40 (s, 2H),
6.41 (d, J = 8.66 Hz, 1H), 6.53–6.59 (m, 2H), 7.04–7.34 (m, 9H); FTIR
(Neat): cmÀ1 520, 754, 806, 972, 1088, 1159, 1202, 1241, 1267,
1295, 1352, 1452, 1506, 1655, 2372, 2853, 2927, 3029, 3406,
3754; FAB-MS: 450 (M)+. Anal. Calcd for C27H31ClN2O2: C, 71.90;
H, 6.93; N, 6.21%. Found: C, 72.19; H, 7.12; N, 6.57%.
4.6.9. 1-(Benzylmethylamino)-3-(1-benzyl-1,2,3,4-
tetrahydroquinolin-6-yloxy)propan-2-ol (17)
1-Benzyl-6-oxiranylmethoxy-1,2,3,4-tetrahydroquinoline (8;
0.295 g, 1 mmol) was coupled with benzylmethylamine (0.12 g,
1 mmol) using general procedure 1; oil; Yield: 0.15 g (37.3%). 1H
NMR (CDCl3, 200 MHz): d 1.96–2.01 (m, 2H), 2.26 (s, 3H), 2.53–
2.62 (m, 2H), 2.78 (t, J = 6.34 Hz, 2H), 3.28 (t, J = 5.61 Hz, 2H),
3.87 (d, J = 5.06 Hz, 2H), 4.05–4.15 (m, 1H), 4.40 (s, 2H), 5.28 (s,
2H), 6.42 (d, J = 8.67 Hz, 1H), 6.54–6.62 (m, 2H), 7.21–7.31 (m,
10H); FTIR (Neat): cmÀ1 626, 700, 740, 798, 869, 975, 1027,
1157, 1201, 1241, 1268, 1350, 1451, 1506, 1601, 1661, 1812,
1954, 2372, 1843, 2929, 3028, 3427, 3778; FAB-MS: 416 (M)+. Anal.
Calcd for C27H32N2O2: C, 77.85; H, 7.74; N, 7.68%. Found: C, 77.35;
H, 8.07; N, 7.89%.
4.6.5. 1-(1-Benzyl-1,2,3,4-tetrahydroquinolin-6-yloxy)-3-(2-p-
tolylethylamino)-propan-2-ol (13)
1-Benzyl-6-oxiranylmethoxy-1,2,3,4-tetrahydroquinoline
(8;
0.295 g, 1 mmol) was coupled with 2-p-tolylethylamine (0.135 g,
1 mmol) using general procedure 1 to afford the title compound
13 as oil. Yield: 0.32 g (71.1%); 1H NMR (CDCl3, 200 MHz): d
1.96–2.01 (m, 2H), 2.30 (s, 3H), 2.74–2.93 (m, 8H), 3.29 (t,
J = 5.47 Hz, 2H), 3.85–3.87 (m, 2H), 4.03–4.05 (m, 1H), 4.40 (s,
2H), 6.40 (d, J = 8.73 Hz,1H), 6.51–6.59 (m, 2H), 7.09 (bs, 5H),
7.25–7.35 (m, 4H); FTIR (Neat): cmÀ1 497, 556, 668, 764, 881,
973, 1057, 1120, 1216, 1268, 1355, 1454, 1509, 1657, 2342,
2366, 2403, 2859, 2929, 3017, 3406, 3677, 3754, 4213; FAB-MS:
m/z 430 (M)+. Anal. Calcd for C28H34N2O2: C, 78.10; H, 7.96; N,
6.51%. Found: C, 78.35; H, 7.83; N, 6.32%.
4.6.10. 1-(4-Benzylpiperazin-1-yl)-3-(1-benzyl-1,2,3,4-
tetrahydroquinolin-6-yloxy)-propan-2-ol (18)
1-Benzyl-6-oxiranylmethoxy-1,2,3,4-tetrahydroquinoline (8;
0.20 g, 0.67 mmol) was coupled with 1-benzylpiperazine (0.13 g,
0.67 mmol) using general procedure 1 to afford the title compound
18 as oil. Yield: 0.18 g (56.3%); 1H NMR (CDCl3, 200 MHz): d 1.26–
2.04 (m, 2H), 2.48–2.68 (m, 10H), 2.78 (t, J = 6.31 Hz, 2H), 3.28 (t,
J = 5.56 Hz, 2H), 3.87 (d, J = 4.86 Hz, 2H), 4.00–4.02 (m, 1H), 4.40
(s, 2H), 5.27 (m, 2H), 6.42 (d, J = 8.70 Hz, 1H), 6.55–6.62 (m, 2H),
7.21–7.30 (m, 10H); FTIR (Neat): cmÀ1 467, 607, 700, 742, 799,
828, 877, 940, 1010, 1059, 1155, 1202, 1241, 1269, 2347, 1452,
1506, 1601, 1661, 1746, 1811, 1952, 2340, 2373, 2815, 2932,
3028, 3404, 3780; FAB-MS: 472 (M+1)+. Anal. Calcd for
C30H37N3O2: C, 76.40; H, 7.91; N, 8.91%. Found: C, 76.77; H, 7.83;
N, 8.73%.
4.6.6. 1-(1-Benzyl-1,2,3,4-tetrahydroquinolin-6-yloxy)-3-
propylaminopropan-2-ol (14)
1-Benzyl-6-oxiranylmethoxy-1,2,3,4-tetrahydroquinoline
(8;
0.295 g, 1 mmol) was coupled with propylamine (0.026 g, 1 mmol)
using general procedure 1 to afford the title compound 14 as solid.
Yield: 0.11 g (31.1%), mp: 80–83 °C. 1H NMR (CDCl3, 200 MHz): d
0.90–0.98 (m, 3H), 1.56–1.71 (m, 2H), 1.96–2.00 (m, 2H), 2.74–
3.04 (m, 6H), 3.26–3.30 (m, 2H), 3.95–4.01 (m, 2H), 4.18–4.20
(m, 1H), 4.40 (s, 2H), 6.40 (d, J = 5.8 Hz,1H), 6.47–6.83 (m, 2H),
7.26 (bs, 5H); FTIR (KBr): cmÀ1 668, 762, 976, 1060, 1158, 1218,
1268, 1353, 1456, 1508, 1621, 2340, 2364, 2337, 3012, 3399;
FAB-MS: m/z 354 (M)+. Anal. Calcd for C22H30N2O2: C, 74.54; H,
8.53; N, 7.90%. Found: C, 74.32; H, 8.67; N, 7.94%.
4.6.11. 1-(1-Benzyl-1,2,3,4-tetrahydroquinolin-6-yloxy)-3-
dibutylaminopropan-2-ol (19)
1-Benzyl-6-oxiranylmethoxy-1,2,3,4-tetrahydroquinoline (8;
0.20 g, 0.67 mmol) was coupled with dibutylamine (0.09 g,
0.67 mmol) using general procedure 1 to afford the title compound
19 as oil. Yield: 0.17 g (59.1%). 1H NMR (CDCl3, 200 MHz): d 0.87–
0.94 (m, 6H), 1.28–1.47 (m, 8H), 1.92–2.09 (m, 2H), 2.35–2.56 (m,
6H), 2.76 (t, J = 6.38 Hz, 2H), 3.28 (t, J = 5.61 Hz, 2H), 3.80–4.01 (m,
3H), 4.40 (s, 2H), 6.43 (d, J = 8.67 Hz, 1H), 6.56–6.64 (m, 2H), 7.21–
7.30 (m, 5H); FTIR (Neat): cmÀ1 667, 698, 757, 867, 940, 1060,
1162, 1203, 1240, 1268, 1295, 1351, 1455, 1508, 1603, 2370,
2866, 2932, 3010, 3406, 3657, 3782; FAB-MS: m/z 424 (M+1)+.
Anal. Calcd for C27H40N2O2: C, 76.37; H, 9.50; N, 6.60%. Found: C,
76.56; H, 9.68; N, 6.35%.
4.6.7. 1-(1-Benzyl-1,2,3,4-tetrahydroquinolin-6-yloxy)-3-
isopropylaminopropan-2-ol (15)
1-benzyl-6-oxiranylmethoxy-1,2,3,4-tetrahydroquinoline
(8;
0.295 g, 1 mmol) was coupled with isopropylamine (0.026 g,
1 mmol) using general procedure 1 to afford the title compound
15 as oil. Yield: 0.13 g (42.3%).1H NMR (CDCl3, 200 MHz): d 1.20–
1.33 (m, 6H), 1.96–2.00 (m, 2H), 2.76 (t, J = 5.87 Hz., 2H), 2.86–
3.09 (m, 2H), 3.28 (t, J = 4.96 Hz., 2H), 3.80–3.94 (m, 2H), 4.18
(bs, 1H), 4.4 (s, 2H), 4.73 (bs, 1H), 6.40 (d, J = 8.56 Hz, 1H), 6.53–
6.60 (m, 2H), 7.27 (bs, 5H); FTIR (Neat): cmÀ1 668, 766, 1060,
1217, 1351,1454, 1508, 1639, 2341, 2367, 2932, 3015, 3436,
3754, 3806, 3906; FAB-MS: m/z 354 (M+1)+. Anal. Calcd for
C22H30N2O2: C, 74.54; H, 8.53; N, 7.90%. Found: C, 74.78; H, 8.76;
N, 8.05%.
4.6.12. 1-(1-Benzyl-1,2,3,4-tetrahydroquinolin-6-yloxy)-3-[4-
(4-nitrophenyl)piperazin-1-yl]propan-2-ol (20)
1-Benzyl-6-oxiranylmethoxy-1,2,3,4-tetrahydroquinoline (8;
0.20 g, 0.67 mmol) was coupled with 1-(4-nitrophenyl)piperazine
(0.14 g, 0.67 mmol) using general procedure 1 to afford the title
compound 20 as oil. Yield: 0.18 g (52.8%); 1H NMR (CDCl3,
200 MHz): d 1.97–2.06 (m, 2H), 2.60–2.70 (m, 4H), 2.76–7.82 (m,
4H), 3.30 (t, J = 5.50 Hz, 2H), 3.41–3.46 (m, 4H), 3.90–3.93 (m,
2H), 4.07–4.11 (m, 1H), 4.41 (s, 2H), 6.43 (d, J = 8.68 Hz, 1H),
6.56–6.63 (m, 2H), 6.80–6.84 (m, 2H), 7.22–7.35 (m, 5H), 8.10–
8.19 (m, 2H); FTIR (Neat): cmÀ1 501, 538, 668, 694, 746, 797,
828, 921, 1000, 1061, 1110, 1164, 1199, 1242, 1265, 1324, 1452,
1493, 1597, 2341, 2367, 2832, 2940, 3431, 3753, 3823; FAB-MS:
m/z 503 (M+1)+. Anal. Calcd for C29H34N4O4: C, 69.30; H, 6.82; N,
11.15%. Found: C, 69.62; H, 6.96; N, 10.98%.
4.6.8. 1-(1-Benzyl-1,2,3,4-tetrahydroquinolin-6-yloxy)-3-(1-
phenylethylamino)-propan-2-ol (16)
1-Benzyl-6-oxiranylmethoxy-1,2,3,4-tetrahydroquinoline
(8;
0.295 g, 0.01 mol) was coupled with 1-phenylethylamine
(0.121 g, 1 mmol) using general procedure 1 to afford the title
compound 16 as oil. Yield: 0.15 g (36.0%). 1H NMR (CDCl3,
200 MHz): d 1.38 (d, J = 3.23 Hz, 3H), 1.85–1.94 (m, 2H), 2.47–
2.72 (m, 5H), 3.21 (t, J = 5.41 Hz, 2H), 3.78 (bs, 2H), 3.95 (bs, 1H),
4.33 (s, 1H), 4.40 (s, 2H), 6.32 (d, J = 8.68 Hz, 1H), 6.70 (d,
J = 12.42 Hz, 2H), 7.23 (bs, 10H); FTIR (Neat): cmÀ1 667, 699, 760,
847, 974, 1061, 1115, 1158, 1217, 1240, 1268, 1296, 1353, 1453,
1508, 1646, 2363, 2931, 3011, 3419; FAB-MS: m/z 416 (M+). Anal.
Calcd for C27H32N2O2: C, 77.85; H, 7.74; N, 6.73%. Found: C, 77.62;
H, 7.95; N, 7.02%.
4.6.13. 1-(1-Benzyl-1,2,3,4-tetrahydroquinolin-6-yloxy)-3-
diethylaminopropan-2-ol (21)
1-Benzyl-6-oxiranylmethoxy-1,2,3,4-tetrahydroquinoline (8;
0.20 g, 0.67 mmol) was coupled with diethylamine (0.05 g,