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A. JAMAL ABDUL NASSER et al.
3-[(1-Methyl-2, 6-diphenylpiperidin-4-ylidene) amino]-2-thioxo-imidazolidin-4-one (3a)
IR(KBr cm-1 ): 3084(NH),1722(C=O), 1664 (C=N),1495(C=S); ¹H NMR -(DMSO-d6, δ (ppm) ):
δ10.32(s,1H NH), 7.58-7.21(m,4H,Ar-H), 3.90(s,2H, 5CH2), 3.54 (s, 2H, 2,6-H in pipridine ring),
2.41(s,2H,3,5-H in pipridine ring) 2.18 (s,3H, N-CH3), Elemental analysis: Calculated for
C21H22N4OS : C,66.58; H,5.81;N,14.79;S,16.90; Found: C, 66.55; H, 5.79; N, 14.75; S, 16.88%.
3-{[2,6-Bis(4-chlorophenyl)-1-methylpiperidin-4-ylidene]amino}-2-thioxo-imidazolidin-4-
one (3b)
IR(KBr, cm -1 ): 3021(NH), 1723(C=O), 1666(C=N), 1520(C=S), 751 (Ar–Cl); ¹H NMR-
(DMSO-d6, δ (ppm)): δ10.23(s,1H NH), 7.58-7.31(m,4H,Ar-H), 3.42(s,2H, 5CH2), 3.54 (s,
2H, 2,6-H in pipridine ring), 2.41(s,2H,3,5-H in pipridine ring), 2.12 (s,3H, N-CH3);
Elemental analysis: Calculated for For C21H20Cl2N4OS : C,56.32; H,4.47;N,12.51;S,7.15;
Found: C,56.30; H,4.42; N,12.54; S,7.12%.
3-{[2,6-Bis(4-hydroxy phenyl)-1-methylpiperidin-4-ylidene]amino}-2-thioxo-imidazolidin-
4-one (3c)
IR(KBr, cm -1 ): 3032(NH), 1722(C=O), 1664 (C=N), 1459(Ar-OH), 1432(C=S); ¹H NMR-
(DMSO-d6, δ (ppm) ): δ11.21 (s,1H,Ar-OH), δ10.11(s,1H, NH), 7.58-7.11(m,4H,Ar-H),
4.21(s,2H, 5CH2), 3.54 (s, 2H, 2,6-H in pipridine ring), 2.20 (s,3H, N-CH3); 2.41(s,2H,3,5-
H in pipridine ring), 2.20 (s,3H, N-CH3); Elemental analysis: Calculated for C21H22N4O3S :C,
61.39; H,5.35;N,13.64;S,7.79; Found: C,61.28; H,5.32; N,13.61; S,7.75%.
3-{[2,6-Bis(4-methoxy phenyl)-1-methylpiperidin-4-ylidene]amino}-2-thioxo-imidazolidin-
4-one (3d)
IR(KBr, cm -1 ): 3051(NH), 1783(C=O), 1675 (C=N), 1432 (C=S); ¹H NMR-(DMSO-d6, δ
(ppm) ): δ10.67(s,1H NH), 7.44-7.21(m,4H,Ar-H), 4.12(s, 3H,Ar-OCH3), 4.07(s,2H, CH2),
3.54 (s, 2H, 2,6-H in pipridine ring), 2.48 (s,3H, N-CH3); 2.41(s,2H,3,5-H in pipridinering);
Elemental analysis: Calculated for C23H26N6O3S:C,62.93; H,5.92;N,19.15;S,7.29; Found:
C,62.90; H,5.93; N,19.12; S,7.25%.
3-{[2,6-Bis(4-nitro phenyl)-1-methylpiperidin-4-ylidene]amino}-2-thioxo-imidazolidin-4-
one (3e)
IR(KBr , cm -1 ): 3014(NH),1742(C=O), 1674(C=N),1553(Ar-NO2),1438(C=S); ¹H NMR -
(DMSO-d6, δ (ppm)): δ10.29(s,1H NH), 7.28-6.97(m,4H,Ar-H), 3.97(s,2H, 5CH2), 2.14
(s,3H, N-CH3); 2.41(s,2H,3,5-H in pipridine ring), 3.54 (s, 2H, 2,6-H in pipridine ring);
Elemental analysis: Calculated for C21H20N6O5S:C,53.79; H,4.26;N,17.93;S,6.83; Found: C,
53.75; H, 4.21; N, 17.90 S, 6.80%.
3-{[2,6-Bis(4-dimethylamine phenyl)-1-methylpiperidin-4-ylidene]amino}-2-
thioxo-imidazolidin-4-one (3f)
IR(KBr,cm-1): 3045(NH), 1736(C=O), 1652 (C=N), 1437(C=S); ¹H NMR(DMSO-d6,
δ(ppm)): 10.69(s,1H NH), 7.42-7.30(m,4H,Ar-H), 3.72(s,2H, 5CH2), 3.54 (s, 2H, 2,6-H in
pipridine ring), 2.79(s,6H,Ar-N(CH3)2), 2.41(s,2H,3,5-H in pipridine ring) , 2.28 (s,3H,
N-CH3); Elemental analysis: Calculated for C25H32N6OS : C,64.56; H,6.88;N,18.07;S,6.88;
Found: C, 64.54; H, 6.85; N, 18.02; S, 6.82%.
Results and Discussion
The IR spectrum of compounds (2a-2f), show an absorption band at 3488-3432, 1676-1616, 1138-
1127 cm-1due to corresponding to the NH2, C=N and C=O groups respectively. The IR spectrum