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Med Chem Res (2012) 21:2807–2822
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3294 (N–H), 2821 (C–H), 1666 (C=O); H NMR (CDCl3,
300 MHz): d 7.3–7.1 (m, 10H, 2Ph), 6.9–6.8 (m, 4H, Ph),
5.2 (s, 1H, N–H, phenytoin), 5.1 (s, 1H, OH) 3.2 (t, 2H,
NCH2–NCH2), 3.1 (m, 4H, piperazine), 2.6 (t, 2H, NCH2–
NCH2), 2.5 (m, 4H, piperazine); 13C NMR (CDCl3): 168.9,
161.2, 143, 129, 128, 126, 116.4, 114.7, 73.3, 58.6, 52.6,
51.8, 43.2; MS (m/z): 457.54 (M ? 1); Anal. calcd for
C27H28N4O3 C, 71.03; H, 6.18; N, 12.27; O, 10.51 Found:
C, 71.24; H, 6.20; N, 12.30; O, 10.46.
(C–H), 1666 (C=O), 1315 (C–N); 1H NMR (CDCl3,
300 MHz): 7.6–7.4 (m, 10H, 2Ph), 6.9–6.4 (m, 4H, Ph), 5.3
(s, 1H, N–H, phenytoin), 3.9 (t, 2H, NCH2–NCH2), 3.7 (m,
4H, piperazine), 2.6 (t, 2H, NCH2–NCH2), 2.4 (m, 4H,
piperazine), 2.2 (s, 3H, CH3); 13C NMR (CDCl3): 168.9,
161.2, 143, 129, 128.4, 126, 116.4, 114.7, 73.3, 58.6, 52.6,
51.8, 43.2, 38.7; MS (m/z): 455.56 (M ? 1); Anal. calcd.
for C27H27N5O4 C, 73.98; H, 6.65; N, 12.33; O, 7.04 cal-
culated: C, 74.27; H, 6.67; N, 12.37; O, 7.06.
5,5-Diphenyl-3-[2-(4-pyridin-2-yl-piperazin-1-yl)-ethyl]-im-
idazolidine-2,4-dione (4f) Melting point: 264–266°C;
yield: 67%; IR (KBr, vmax cm-1): 3290, 1599 (N–H), 2831
(C–H), 1315 (C–N); 1H NMR (CDCl3, 300 MHz): d 8.2 (d,
1H, H-1, pyridyl), 7.5–7.3 (m, 10H, 2Ph), 6.6–6.5 (m, 3H,
H-2, H-3, H-4, pyridyl), 5.3 (s, 1H, N–H, phenytoin), 3.1 (t,
2H, NCH2–NCH2), 3.0 (m, 4H, piperazine), 2.6 (t, 2H,
NCH2–NCH2) 2.3 (m, 4H, piperazine); 13C NMR (CDCl3):
168.9, 161.2, 161.1, 148.9, 143, 138, 129, 128, 126, 113,
108, 73.3, 57.9, 55.1, 51.8, 43.2 (1C); MS (m/z): 442.52
(M ? 1); Anal. calcd. for C26H27N5O2; C, 70.73; H, 6.16;
N, 15.86; O, 7.25 Found: C, 70.65; H, 6.15; N, 15.83; O,
7.23%.
3-{2-[4-(4-Fluoro-phenyl)-piperazin-1-yl]-ethyl}-5,5-diphenyl-
imidazolidine-2,4-dione (4b) Melting point: 263–265°C;
yield: 60%; IR (KBr, vmax cm-1): 3306 (N–H), 2825
(C–H), 1685 (C=O); 1H NMR (CDCl3, 300 MHz): d
7.3–7.2 (m, 10H, 2Ph), 6.9–6.8 (m, 4H, Ph), 5.2 (s, 1H,
N–H, phenytoin), 3.9 (t, 2H, NCH2–NCH2), 3.8 (m, 4H,
piperazine), 3.1 (t, 2H, NCH2–NCH2), 2.7 (m, 4H, piper-
azine); 13C NMR (CDCl3): 168.9, 161.2, 143, 129, 128,
126, 116.4, 114.7, 73.3, 58.6, 52.6, 51.8, 43.2; MS (m/z):
459.43 (M ? 1); Anal.calcd. for C27H27FN4O2: C, 70.72;
H, 5.94; N, 12.22; O, 6.98; Found: C, 71.89; H, 5.93; N,
12.26; O, 6.97.
3-{2-[4-(4-Chloro-phenyl)-piperazin-1-yl]-ethyl}-5,5-diphenyl-
imidazolidine-2,4-dione (4c) Melting point: 263-265°C;
yield: 57% IR (KBr, vmax cm-1): 3286 (N–H), 2827 (C–H),
1657 (C=O); 1H NMR (CDCl3, 300 MHz): d 7.3–7.2
(m, 10H, 2Ph), 6.9–6.8 (m, 4H, Ph), 5.3 (s, 1H, N–H,
phenytoin), 3.9 (t, 2H, NCH2–NCH2), 3.7 (m, 4H, pipera-
zine), 3.1 (t, 2H, NCH2–NCH2), 3.0 (s, 4H, piperazine);
13C NMR (CDCl3): 168.9, 161.2, 143, 129, 128, 126,
116.4, 114.7, 73.3, 58.6, 52.6, 51.8, 43.2; MS (m/z): 475.98
(M ? 1); Anal. calcd. for C27H27ClN4O2; C, 68.27; H,
5.73; Cl, 7.46; N, 11.80; O, 6.74; Found: C, 68.54; H, 5.75;
Cl, 7.48; N, 11.84; O, 6.76.
General procedure for the preparation of 3-[(p-aniline)-
ethyl]-5,5-diphenyl imidazolidine-2,4-dione (6)
Steps 1 and 2 are same as described under the preparation
of 3-[(4-arylpiperazin-1-yl)-ethyl]-5,5-diphenyl-imidazoli-
dine-2,4-dione (4).
Step 3: General procedure for the synthesis of compound
(6a–e)
3-(2-Chloro-ethyl)-5,5-diphenylhydantoin 2 (0.005 mol)
along with various para substituted anilines (5a–
f) (0.001 mol) and DMSO were refluxed for appropriate
time till the completion of reaction monitored by TLC
(EtOAc:Hexane 2:1). The solvent was evaporated and the
residue was treated with water (50 ml). The precipitate was
filtered off, washed with water and the crude product
obtained was purified by column chromatography to afford
the products (6a–e).
3-{2-[4-(4-Nitro-phenyl)-piperazin-1-yl]-ethyl}-5,5-diphenyl-
imidazolidine-2,4-dione (4d) Melting point 265-267°C;
yield 62%; IR (KBr, vmax cm-1): 3315 (N–H), 2848 (C–H),
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1667 (C=O); H NMR (CDCl3, 300 MHz): d 8.2–8.1 (d,
2H, Ph), 7.4–6.9 (m, 10H, 2Ph), 6.7–6.6 (s, 2H, Ph) 6.2 (s,
1H, N–H, phenytoin), 3.9 (t, 2H, NCH2–NCH2), 3.8 (m,
4H, piperazine) 3.4 (t, 2H, NCH2–NCH2,), 3.0 (m, 4H,
piperazine); 13C NMR (CDCl3): 166.9, 160.2, 141, 125,
122, 121, 116.4, 114.7, 70.3, 54.6, 50.6, 50.8, 42.2; MS
(m/z): 486.53(M ? 1): Anal. calcd. for C27H27N5O4; C,
66.79; H, 5.61; N, 14.42; O, 13.18 Found: C, 67.05; H,
5.63, N, 14.47; O, 13.23.
3-[2-(4-Hydroxy-phenylamino)-ethyl]-5,5-diphenyl-imida-
zolidine-2,4-dione (6a) Semisolid mass; yield: 65%; IR
(solid run in solution, vmax cm-1): 3456 (OH), 3323 (N–H),
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2918 (C–H), 1655 (C=O), 1315 (C–N); H NMR (CDCl3,
300 MHz): d 7.4–7.1 (m, 10H, 2Ph), 7.3 (m, 4H, 1Ph), 6.1
(s, 1H, N–H, phenytoin), 5.1 (s 1H, OH), 3.9 (s, 1H, N–H,
aniline), 2.9 (t, 2H, NCH2), 2.6 (t, 2H, NCH2); 13C NMR
(CDCl3): 168.9, 161.2, 145.7, 143, 136.1, 129, 128.4, 126,
116.5, 113.7, 73.3, 49.8, 45; MS (m/z): 388.43 (M ? 1):
5,5-Diphenyl-3-[2-(4-p-tolyl-piperazin-1-yl)-ethyl]-imidaz-
olidine-2,4-dione (4e) Semisolid mass; yield: 58%; IR
(solid run in solution, vmax cm-1): 3387 (N–H), 2918
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