Med Chem Res (2012) 21:1–9
7
2-(1-(((Pyridin-2-yl)methyleneamino)methyl)
NMR (DMSO-d6, 400 MHz) d: 11.3 (s, br, 1H, OH), 8.37
(s, 1H, Ar–H), 8.22 (d, 1H, Ar–H), 8.09 (d, 1H, Ar–H),
7.73 (t, 1H, Ar–H), 2.78 (s, 2H, CH2), 2.32 (s, 2H, CH2),
2.15 (s, 3H, CH3), 1.38–1.35 (m, 10H, cyclohexyl meth-
ylenes group). Anal. calcd. for C18H22N2O2 (in %): C,
72.46; H, 7.43; N, 9.39. Found: C, 72.31; H, 7.21; N, 9.58.
cyclohexyl)acetic acid (6k)
The general experimental procedure described above affor-
ded 6k, and the product obtained from gabapentin (3)
(1.72 g, 0.01 mol) and 2-pyridine carboxaldehyde (4k)
(1.10 g, 0.01 mol). FT-IR (KBr, cm-1) m: 3024 (C–H), 2924
1
(O–H), 1701 (C=N), 1461 (C=C), 1073 (C–N). H NMR
2-(1-((1-(1H-indol-3-yl)ethylideneamino)methyl)
(DMSO-d6, 400 MHz) d: 11.3 (s, br, 1H, OH), 8.76 (d, 1H,
pyridine-H), 8.11 (d, 1H, pyridine-H), 7.92 (t, 1H, pyridine-
H), 7.83 (t, 1H, pyridine-H), 6.97 (s, 1H, CH), 2.76 (s, 2H,
CH2), 2.30 (s, 2H, CH2), 1.38–1.35 (m, 10H, cyclohexyl
methylenes group). Anal. calcd. for C15H20N2O2 (in %): C,
69.20; H, 7.74; N, 10.76. Found: C, 69.54; H, 7.59; N, 10.41.
cyclohexyl)acetic acid (7d)
The general experimental procedure described above
afforded 7d, and the product obtained from gabapentin (3)
(1.72 g, 0.01 mol) and 1-(1H-indol-3-yl)ethanone (5d)
(1.60 g, 0.01 mol). FT-IR (KBr, cm-1) m: 3058 (C–H),
1
2923 (O–H), 1698 (C=N), 1462 (C=C), 1083 (C–O). H
2-(1-((1-(4-Ethoxyphenyl)ethylideneamino)methyl)
NMR (DMSO-d6, 400 MHz) d: 11.2 (s, br, 1H, OH), 9.27
(s, 1H, NH), 7.52 (d, 1H, Ar–H), 7.43 (d, 1H, Ar–H), 7.31
(s, 1H, pyrrole-H), 7.13 (t, 1H, Ar–H), 7.10 (t, 1H, Ar–H),
2.75 (s, 2H, CH2), 2.28 (s, 2H, CH2), 2.13 (s, 3H, CH3),
1.36–1.32 (m, 10H, cyclohexyl methylenes group). Anal.
calcd. for C19H24N2O2 (in %): C, 73.05; H, 7.74; N, 8.97.
Found: C, 72.81; H, 7.92; N, 9.12.
cyclohexyl)acetic acid (7a)
The general experimental procedure described above
afforded 7a, and the product obtained from gabapentin (3)
(1.72 g, 0.01 mol) and 1-(4-ethoxyphenyl)ethanone (5a)
(1.65 g, 0.01 mol). FT-IR (KBr, cm-1) m: 3075 (C–H),
1
2924 (O–H), 1699 (C=N), 1461 (C=C), 1091 (C–N). H
NMR (DMSO-d6, 400 MHz) d: 11.1 (s, br, 1H, OH),
7.57–7.41 (d, 2H, Ar–H), 6.91–6.43 (d, 2H, Ar–H), 3.75
(q, 2H, CH2), 2.76 (s, 2H, CH2), 2.29 (s, 2H, CH2), 2.34
(t, 3H, CH3), 2.14 (s, 3H, CH3), 1.37–1.35 (m, 10H, cyclo-
hexyl methylenes group). Anal. calcd. for C19H27NO3 (in %):
C, 71.89; H, 8.57; N, 4.41. Found: C, 71.85; H, 8.59; N, 4.21.
2-(1-((1-(Pyridin-3-yl)ethylideneamino)methyl)
cyclohexyl)acetic acid (7e)
The general experimental procedure described above
afforded 7e, and the product obtained from gabapentin (3)
(1.72 g, 0.01 mol) and 1-(pyridin-3-yl)ethanone (5e)
(1.22 g, 0.01 mol). FT-IR (KBr, cm-1) m: 3012 (C–H), 2924
1
2-(1-((1-(Pyridin-2-yl)ethylideneamino)methyl)
(O–H), 1698 (C=N), 1461 (C=C), 1088 (C–N). H NMR
cyclohexyl)acetic acid (7b)
(DMSO-d6, 400 MHz) d: 11.3 (s, br, 1H, OH), 9.21 (s, 1H,
pyridine-H), 8.81 (d, 1H, pyridine-H), 8.37 (d, 1H, pyridine-
H), 7.51 (t, 1H, pyridine-H), 2.77 (s, 2H, CH2), 2.29 (s, 2H,
CH2), 2.14 (s, 3H, CH3), 1.38–1.36 (m, 10H, cyclohexyl
methylenes group). Anal. calcd. for C16H22N2O2 (in %): C,
70.04; H, 8.08; N, 10.21. Found: C, 70.31; H, 8.21; N, 10.38.
The general experimental procedure described above
afforded 7b, and the product obtained from gabapentin (3)
(1.72 g, 0.01 mol) and 1-(pyridin-2-yl)ethanone (5b)
(1.22 g, 0.01 mol). FT-IR (KBr, cm-1) m: 3083 (C–H), 2924
1
(O–H), 1706 (C=N), 1461 (C=C), 1068 (C–N). H NMR
(DMSO-d6) d: 11.31 (s, br, 1H, OH), 8.73 (d, 1H, pyridine-
H), 8.01 (d, 1H, pyridine-H), 7.81 (t, 1H, pyridine-H), 7.63
(t, 1H, pyridine-H), 2.78 (s, 2H, CH2), 2.32 (s, 2H, CH2),
2.14 (s, 3H, CH3), 1.38–1.34 (m, 10H, cyclohexyl methyl-
enes group). Anal. calcd. for C16H22N2O2 (in %): C, 70.04;
H, 8.08; N, 10.21. Found: C, 70.21; H, 8.22; N, 10.44.
2-(1-((1-(Naphthalen-2-yl)ethylideneamino)methyl)
cyclohexyl)acetic acid (7f)
The general experimental procedure described above
afforded 7f, and the product obtained from gabapentin (3)
(1.72 g, 0.01 mol) and 1-(naphthalen-2-yl)ethanone (5f)
(1.71 g, 0.01 mol). FT-IR (KBr, cm-1) m: 3062 (C–H),
1
2-(1-((1,3-Acetylbenzonitrilethylideneamino)
2923 (O–H), 1699 (C=N), 1461 (C=C), 1075 (C–N). H
methyl)cyclohexyl)acetic acid (7c)
NMR (DMSO-d6, 400 MHz) d: 11.1 (s, br, 1H, OH), 8.50
(s, 1H, Ar–H), 7.41 (d, 1H, Ar–H), 7.31 (d, 1H, Ar–H),
7.20–7.13 (d, 2H, Ar–H), 7.08–6.96 (t, 2H, Ar–H), 2.79
(s, 2H, CH2), 2.28 (s, 2H, CH2), 2.14 (s, 3H, CH3), 1.37–1.35
(m, 10H, cyclohexyl methylenes group). Anal. calcd. for
C21H25NO2 (in %): C, 77.98; H, 7.79; N, 4.33. Found: C,
78.24; H, 7.54; N, 4.52.
The general experimental procedure described above
afforded 7c, and the product obtained from gabapentin (3)
(1.72 g, 0.01 mol) and 3-acetylbenzonitrile (5c) (1.46 g,
0.01 mol). FT-IR (KBr, cm-1) m: 3056 (C–H), 2924 (O–H),
1
2360 (C:N), 1699 (C=N), 1461 (C=C), 1078 (C–N). H
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