Med Chem Res
was then filtered, washed with cold water, dried and puri-
fied by column chromatography.
130.3, 129.1, 128.7, 128.33, 127.3, 126.0, 123.5, 113.3,
70.8, 53.4, 47.7, 44.4, 43.0, 38.0, 31.4; C H N O :
3
5 33 3 3
m/z (543.6).
3-(2-Oxo-2-(4-(piperidin-1-yl)phenyl)ethyl)-5,5-
diphenylimidazolidine-2,4-dione (13)
3-(2-Oxo-2-(4-(4-phenylpiperazin-1-yl)phenyl)ethyl)-5,5-
diphenylimidazolidine-2,4-dione (17)
Yellow crystals, MP 265–266 °C, 69 % yield (CH Cl ); IR
KBr, cm ) m: 3177 (NH), 1775, 1719, 1676 (C=O); H
2
2
-
1
1
(
Yellow powder, MP 259–260 °C, 59 % yield (MeOH); IR
-1 1
(KBr, cm ) m: 3214 (NH), 1777, 1715, 1673 (C=O); H
NMR (DMSO-d ): d 7.78 (d, 2H, J = 9.0 Hz), 7.42 (d, 4H,
6
J = 7.0 Hz), 7.30–7.26 (m, 6H), 6.78 (s, 2H), 6.62 (s, 1H),
NMR (DMSO-d ): d 8.14 (s, 1H), 7.83 (d, 2H,
6
1
3
4
.84 (s, 2H), 3.30 (s, 4H), 1.59 (s, 6H); C NMR (DMSO-
d6): d 188.0, 173.7, 156.1, 154.6, 139.1, 130.3, 128.7,
28.5, 127.3, 123.4, 113.2, 70.8, 48.4, 44.4, 25.2, 24.3;
C H N O : m/z (453.5).
J = 9.0 Hz), 7.45–7.37 (m, 6H), 7.33–7.28 (m, 6H), 6.83
(d, 2H, J = 9.0 Hz), 6.62 (d, 2H, J = 7.0 Hz), 6.22 (s,
1
1H), 4.84 (s, 2H), 3.66 (s, 4H), 3.46 (s, 4H); C NMR
3
1
(DMSO-d ): d 188.2, 173.6, 155.9, 154.3, 139.0, 130.2,
2
8
27
3
3
6
128.7, 128.6, 127.3, 124.4, 113.7, 113.2, 70.8, 63.4, 46.6,
3-(2-(4-Morpholinophenyl)-2-oxoethyl)-5,5-
diphenylimidazolidine-2,4-dione (14)
44.7, 44.5; C H N O : m/z (529.8).
33 30 4 3
3-(2-(4-(4-(2-Ethoxyphenyl)piperazin-1-yl)phenyl)-2-
oxoethyl)-5,5-diphenylimidazolidine-2,4-dione (18)
Yellow crystals, MP 271–272 °C, 61 % yield (CH Cl ); IR
KBr, cm ) m: 3176 (NH), 1774, 1717, 1678 (C=O); H
2
2
-
1
1
(
NMR (DMSO-d ): d 8.97 (d, 1H, J = 10 Hz), 7.41 (d, 2H,
J = 8.0 Hz), 7.03 (d, 4H, J = 7.0 Hz), 6.91–6.86 (m, 6H),
Yellow powder, MP 167–168 °C, 55 % yield (MeOH); IR
(KBr, cm ) m: 3170 (NH), 1773, 1711, 1670 (C=O); H
6
-
1
1
6
4
1
4
.44 (d, 2H, J = 8.5 Hz), 4.41 (s, 2H), 2.85 (s, 4H), 2.72 (s,
1
NMR (DMSO-d ): d 7.83 (d, 2H, J = 9.0 Hz), 7.43 (d, 4H,
6
3
H); C NMR (DMSO-d ): d 188.5, 173.5, 155.1, 154.2,
J = 6.5 Hz), 7.32–7.27 (m, 6H), 6.93 (s, 1H), 6.86–6.80
(m, 5H), 6.51 (s, 1H), 4.83 (s, 2H), 4.02 (t, 2H,
6
39.3, 129.6, 128.0, 127.7, 126.9, 123.9, 112.7, 69.8, 65.8,
1
3
6.6, 43.8; C H N O : m/z (455.5).
27 25 3 4
J = 7.0 Hz), 3.47 (s, 4H), 3.15 (s, 4H), 1.40 (s, 3H);
NMR (DMSO-d ): d 188.2, 173.7, 156.0, 154.7, 151.6,
C
6
3-(2-(4-(4-Phenylpiperidin-1-yl)phenyl)-2-oxoethyl)-5,5-
diphenylimidazolidine-2,4-dione (15)
140.8, 139.1, 130.2, 128.7, 128.5, 127.3, 124.4, 123.2,
121.0, 118.2, 113.4, 112.6, 70.8, 63.7, 50.3, 47.4, 44.5,
14.9; C H N O : m/z (574.6).
35 34 4 4
White powder, MP 187–189 °C, 73 % yield (CH Cl ); IR
KBr, cm ) m: 3175 (NH), 1775, 1716, 1676 (C=O); H
2
2
-
1
1
(
3-(2-(4-(4-(2-Chlorophenyl)piperazin-1-yl)phenyl)-2-
oxoethyl)-5,5-diphenylimidazolidine-2,4-dione (19)
NMR (DMSO-d ): d 7.78 (d, 2H, J = 9.0 Hz), 7.39-7.34
6
(
m, 6H), 7.30–7.26 (m, 9H), 7.02 (d, 2H, J = 7.5 Hz), 6.85
s, 1H), 4.79 (s, 2H), 3.80 (d, 2H, J = 13.5 Hz), 2.75 (t,
(
Yellow powder, MP 216–218 °C, 57 % yield (MeOH); IR
(KBr, cm ) m: 3089 (NH), 1773, 1717, 1672 (C=O); H
-
1
1
2
H, J = 12.0 Hz), 2.46 (d, 2H, J = 7.5 Hz), 1.70 (q, 3H,
1
3
J = 13.5 Hz); C NMR (DMSO-d ): d 188.0, 173.7,
NMR (DMSO-d ): d 9.70 (s, 1H), 7.94 (d, 2H,
6
6
1
56.2, 154.4, 139.8, 130.5, 128.9, 128.6, 128.2, 122.9,
J = 8.5 Hz), 7.45–7.38 (m, 11H), 7.33 (t, 1H, J = 7.0 Hz),
7.19 (d, 1H, J = 7.0 Hz), 7.08 (t, 3H, J = 8.0 Hz), 4.93 (s,
1
23.2, 113.3, 70.8, 53.1, 48.1, 44.5, 43.8, 38.6;
1
3
C H N O : m/z (529.0).
3
2H), 3.54 (s, 4H), 3.11 (s, 4H); C NMR (DMSO-d ): d
3
4
31
3
6
189.2, 173.5, 155.1, 154.3, 148.5, 139.6, 130.3, 130.1,
3-(2-(4-(4-Benzylpiperidin-1-yl)phenyl)-2-oxoethyl)-5,5-
diphenylimidazolidine-2,4-dione (16)
128.4, 128.2, 128.1, 127.6, 126.9, 124.2, 123.4, 120.9,
113.1, 69.6, 56.0, 50.5, 46.6, 44.2; C H ClN O :
3
3
29
4 3
m/z (565.0).
Yellow powder, MP 133–135 °C, 66 % yield (CH Cl ); IR
KBr, cm ) m: 3220 (NH), 1774, 1716, 1675 (C=O); H
2
2
-
1
1
(
3-(2-(4-(4-(4-Chlorophenyl)piperazin-1-yl)phenyl)-2-
oxoethyl)-5,5-diphenylimidazolidine-2,4-dione (20)
NMR (DMSO-d ): d 7.76 (d, 2H, J = 9.0 Hz), 7.41 (d, 4H,
6
J = 7.0 Hz), 7.29–7.19 (m, 8H), 7.15–7.10 (m, 1H), 7.07
(
d, 2H, J = 7.0 Hz), 6.86 (s, 1H), 6.75 (d, 2H,
J = 8.0 Hz), 5.18 (s, 2H), 4.78 (s, 2H), 3.81 (d, 2H,
J = 13.0 Hz), 2.76 (t, 2H, J = 12.5 Hz), 2.48 (d, 2H,
Yellow powder, MP 277–279 °C, 57 % yield (MeOH); IR
-1 1
(KBr, cm ) m: 3231 (NH), 1774, 1716, 1674 (C=O); H
NMR (DMSO-d ): d 9.73 (s, 1H), 7.93 (d, 2H,
6
1
3
J = 7.0 Hz), 1.69 (q, 3H, J = 13.5 Hz);
DMSO-d ): d 188.0, 173.7, 156.2, 154.4, 140.1, 139.1,
C NMR
J = 9.0 Hz), 7.43–7.38 (m, 10H), 7.27 (d, 2H,
J = 9.0 Hz), 7.08 (d, 2H, J = 8.5 Hz), 6.99 (s, 2H), 4.92
(
6
1
23