Arch. Pharm. Chem. Life Sci. 2010, 343, 333–341
Anticonvulsant Activity of Certain Succinimides
339
N-[{4-(3-Trifluoromethylphenyl)-piperazin-1-yl}-methyl]-3-
N-[{4-(3-Methylphenyl)-piperazin-1-yl}-methyl]-3-(3-
(2-chlorophenyl)-pyrrolidine-2,5-dione 12
chlorophenyl)-pyrrolidine-2,5-dione 18
White powdery crystals. Yield: 65%; m.p. 118–1208C; 1H-NMR
(300 MHz, CDCl3) d: 2.85–2.93 (m, 5H, 4H piperazine; 1H imide,),
3.23–3.32 (m, 5H, 4H piperazine; 1H imide,), 4.36 (q, 1H, imide, J
= 5.90 Hz), 4.65 (t, 2H, -CH2-, J = 13.33 Hz), 7.05–7.11 (m, 3H, ArH),
7.21–7.43 (m, 5H, ArH). C22H21N3O2Cl1F3 (451.88).
White powdery crystals. Yield: 76%; m.p.: 81–838C; 1H-NMR (300
MHz, CDCl3) d: 2.31 (s, 3H, -CH3), 2.78 (brs, 4H, piperazine), 2.84
(dd, 1H, imide, J = 5.13 Hz, J = 18.72 Hz), 3.16 (t, 4H, piperazine, J
= 4.99 Hz), 3.23 (dd, 1H, imide, J = 9.49 Hz, J = 18,46 Hz), 4.03 (q,
1H, imide, J = 5.13 Hz), 4.60 (t, 2H, -CH2-, J = 13.59 Hz), 6.68–6.73
(m, 3H, ArH), 7.09–7.18 (m, 2H, ArH), 7.29–7.34 (m, 3H, ArH).
C22H24N3O2Cl1 (397.90).
Monohydrochloride N-[{4-(2-fluorophenyl)-piperazin-1-
yl}-methyl]-3-(3-chlorophenyl)-pyrrolidine-2,5-dione 13
N-[{4-(2-Methoxyphenyl)-piperazin-1-yl}-methyl]-3-(3-
1
White powdery crystals. Yield: 72%; m.p.: 157–1598C; H-NMR
chlorophenyl)-pyrrolidine-2,5-dione 19
(300 MHz, CDCl3) d: 2.92 (dd, 1H, imide, J = 6.41 Hz, J = 17.95 Hz),
3.06 (brs, 4H, piperazine), 3.21–3.48 (m, 5H, 4H piperazine; 1H
imide), 4.37 (q, 1H, imide, J = 6.15 Hz), 4.70 (s, 2H, -CH2-), 6.97–
7.19 (m, 3H, ArH), 7.34–7.40 (m, 4H, ArH), 7.56 (s, 1H, ArH), 11.36
(s, 1H, HCl). C21H22N3O2Cl2F1 (438.34).
White powdery crystals. Yield: 67%; m.p.: 99–1018C; 1H-NMR
(300 MHz, CDCl3) d: 2.85–2.89 (m, 5H, 4H piperazine; 1H imide),
3.09 (brs, 4H, piperazine), 3.25 (dd, 1H, imide, J = 9.49 Hz, J =
18.46 Hz), 3.85 (s, 3H, -OCH3), 4.07 (q, 1H, imide, J = 5.39 Hz), 4.62
(t, 2H, -CH2-, J = 13.20 Hz), 6.85–7.03 (m, 4H, ArH), 7.16 (d, 1H,
ArH, J = 6.15 Hz), 7.29–7.36 (m, 3H, ArH). C22H24N3O3Cl1 (413.90).
N-[{4-(2-Chlorophenyl)-piperazin-1-yl}-methyl]-3-(3-
chlorophenyl)-pyrrolidine-2,5-dione 14
N-[{4-(2-Chlorophenyl)-piperazin-1-yl}-methyl]-3-(4-
White powdery crystals. Yield: 78%; m.p. 95–978C; 1H-NMR (300
MHz, CDCl3) d: 2.85 (brs, 4H, piperazine), 2.91 (dd, 1H, imide, J =
5.13 Hz, J = 18.35 Hz), 3.06 (brs, 4H, piperazine), 3.28 (dd, 1H,
imide, J = 9.75 Hz, J = 18.46 Hz), 4.08 (q, 1H, imide, J = 5.13 Hz),
4.62 (t, 2H, -CH2-, J = 13.34 Hz), 6.94–7.04 (m, 2H, ArH), 7.14–7.36
(m, 6H, ArH). C21H21N3O2Cl2 (418.33).
chlorophenyl)-pyrrolidine-2,5-dione 20
1
White powdery crystals. Yield: 72%; m.p.: 114–1168C; H-NMR
(300 MHz, CDCl3) d: 2.82 (brs, 4H, piperazine), 2.89 (dd, 1H,
imide, J = 5.13 Hz, J = 18.46 Hz), 3.05 (brs, 4H, piperazine), 3.27
(dd, 1H, imide, J = 9.74 Hz, J =18.46 Hz), 4.07 (q, 1H, imide, J = 5.13
Hz), 4.61 (t, 2H, -CH2-, J = 13.34 Hz), 6.94–7.04 (m, 2H, ArH), 7.18–
7.24 (m, 3H, ArH), 7.33–7.39 (m, 3H, ArH). C21H21N3O2Cl2 (418.33).
N-[{4-(3-Chlorophenyl)-piperazin-1-yl}-methyl]-3-(3-
chlorophenyl)-pyrrolidine-2,5-dione 15
N-[{4-(3-Chlorophenyl)-piperazin-1-yl}-methyl]-3-(4-
White powdery crystals Yield: 67%; m.p.: 81–838C; 1H-NMR (300
MHz, CDCl3) d: 2.78 (brs, 4H, piperazine), 2.86 (dd, 1H, imide, J =
5.38 Hz, J = 18.72 Hz), 3.18 (t, 4H, piperazine, J = 4.87 Hz), 3.24
(dd, 1H, imide, J = 9.74 Hz, J =18.72 Hz), 4.05 (q, 1H, imide, J = 5.13
Hz), 4.60 (t, 2H, -CH2-, J = 13.59 Hz), 6.76–6.85 (m, 4H, ArH), 7.10–
7.18 (m, 2H, ArH), 7.30–7.35 (m, 2H, ArH). C21H21N3O2Cl2 (418.33).
chlorophenyl)-pyrrolidine-2,5-dione 21
1
White powdery crystals. Yield: 70%; m.p.: 120–1228C; H-NMR
(300 MHz, CDCl3) d: 2.79 (brs, 4H, piperazine), 2.85 (dd, 1H,
imide, J = 5.13 Hz, J = 18.46 Hz), 3.19 (brs, 4H, piperazine), 3.25
(dd, 1H, imide, J = 9.49 Hz, J = 18.46 Hz), 4.05 (q, 1H, imide, J =
5.13 Hz), 4.60 (s, 2H, -CH2-), 6.76–6.97 (m, 3H, ArH), 7.14–7.23 (m,
3H, ArH), 7.33–7.37 (m, 2H, ArH). C21H21N3O2Cl2 (418.33).
N-[{4-(4-Chlorophenyl)-piperazin-1-yl}-methyl]-3-(3-
chlorophenyl)-pyrrolidine-2,5-dione 16
N-[{4-(4-Chlorophenyl)-piperazin-1-yl}-methyl]-3-(4-
1
White powdery crystals. Yield: 70%; m.p.: 113–1158C; H-NMR
chlorophenyl)-pyrrolidine-2,5-dione 22
(300 MHz, CDCl3) d: 2.74–2.78 (m, 4H, piperazine), 2.85 (dd, 1H,
imide, J = 5.38 Hz, J = 18.72 Hz), 3.13 (t, 4H piperazine, J = 4.87
Hz), 3.24 (dd, 1H, imide, J = 9.49 Hz, J = 18.46 Hz), 4.03 (q, 1H,
imide, J = 5.13 Hz), 4.59 (t, 2H, -CH2-, J = 13.59 Hz), 6.78–6.86 (m,
2H, ArH), 7.10–7.13 (m, 1H, ArH), 7.16–7.21 (m, 2H, ArH), 7.30–
7.34 (m, 3H, ArH). C21H21N3O2Cl2 (418.33).
1
White powdery crystals. Yield: 75%; m.p.: 115–1178C; H-NMR
(300 MHz, CDCl3) d: 2.78 (brs, 4H, piperazine), 2.84 (dd, 1H,
imide, J = 5.13 Hz, J = 18.46 Hz), 3.14 (t, 4H, piperazine, J = 5.00
Hz), 3.24 (dd, 1H, imide, J = 9.74 Hz, J = 18.72 Hz), 4.04 (q, 1H,
imide, J = 5.13 Hz), 4.59 (t, 2H, -CH2-, J = 13.37 Hz), 6.83 (d, 2H,
ArH, J = 8.72 Hz), 7.16–7.22 (m, 4H, ArH), 7.33–7.37 (m, 2H, ArH).
C21H21N3O2Cl2 (418.33).
Monohydrochloride N-[{4-(3-trifluoromethylphenyl)-
piperazin-1-yl}-methyl]-3-(3-chlorophenyl)-pyrrolidine-
2,5-dione 17
N-[{4-(3-Trifluoromethylphenyl)-piperazin-1-yl}-methyl]-3-
(4-chlorophenyl)-pyrrolidine-2,5-dione 23
1
White powdery crystals. Yield: 63%; m.p.: 168–1708C; H-NMR
White powdery crystals. Yield: 68%; m.p.: 87–898C; 1H-NMR (300
MHz, CDCl3) d: 2.80 (brs, 4H, piperazine), 2.85 (dd, 1H, imide, J =
5.13 Hz, J = 18.46 Hz), 3.20 (brs, 4H, piperazine), 3.25 (dd, 1H,
imide, J = 9.74 Hz, J =18.46 Hz), 4.05 (q, 1H, imide, J = 5.13 Hz),
4.60 (t, 2H, -CH2-, J = 13.33 Hz), 7.03–7.19 (m, 3H, ArH), 7.20–7.24
(m, 2H, ArH), 7.31–7.37 (m, 3H, ArH). C22H21N3O2Cl1F3 (451.88).
(300 MHz, CDCl3) d: 2.92 (dd, 1H, imide, J = 6.41 Hz, J = 17.95 Hz),
3.22–3.45 (m, 5H, 1H imide; 4H piperazine), 3.57 (brs, 4H, pipera-
zine), 4.37 (q, 1H, imide, J = 6.41 Hz), 4.75 (s, 2H, -CH2-), 7.09–7.15
(m, 1H, ArH), 7.21–7.32 (m, 2H, ArH), 7.34–7.45 (m, 5H, ArH),
11.35 (brs, 1H, HCl). C22H22N3O2Cl2F3 (488.35).
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