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15.78%. 1H NMR: {CDCl3, 400 MHz, d (ppm)} 0.80–0.90
(m, 6H), 1.53–1.61 (m, 4H), 1.83–1.88 (m, 1H), 1.99–2.04
(m, 1H), 2.49–2.71 (m, 6H), 3.24–3.26 (m, 4H), 4.49–4.55
(m, 1H), 6.76–6.80 (d, 2H), 7.41–7.44 (d, 2H). Elemental
analysis: calcd for C20H27N3O2: C, 70.35; H, 7.97; N,
12.31. Found: C, 70.07; H, 8.03; N, 12.11%.
HPLC analysis: [95% purity using two different mobile
phases.
3,3-Diethyl-4,5-dihydro-5-(4-[4-hydroxyphenyl]piperazi-
nylmethyl)-2(3H)-furanone (15) Pale yellow solid. Yield:
1
7.79%. H NMR: {CDCl3, 400 MHz, d (ppm)} 0.85–0.92
(m, 6H), 1.55–1.62 (m, 4H), 1.82–1.88 (m, 1H), 2.01–2.06
(m, 1H), 2.54–2.81 (m, 6H), 3.02–3.05 (m, 4H), 4.55–4.62
(m, 1H), 6.71 (d, 2H), 6.78 (d, 2H). LC–MS (ESI)
(m/z) 333.0 (M ? H)?. HPLC analysis:[95% purity using
two different mobile phases.
3,3-Diethyl-4,5-dihydro-5-(4-[4-nitrophenyl]piperazinylm-
ethyl)-2(3H)-furanone (10) Pale yellow liquid. Yield:
25.97%. 1H NMR: {CDCl3, 400 MHz, d (ppm)} 0.87–0.97
(m, 6H), 1.59–1.66 (m, 4H), 1.89–1.94 (m, 1H), 2.05–2.10
(m, 1H), 2.56–2.78 (m, 6H), 3.37–3.42 (m, 4H), 4.55–4.61
(m, 1H), 6.77–6.82 (d, 2H), 8.07–8.12 (d, 2H). LC–MS
(ESI) (m/z) 362.3 (M ? H)?. HPLC analysis:[95% purity
using two different mobile phases.
3,3-Diethyl-4,5-dihydro-5-(4-[2-hydroxyphenyl]piperazi-
nylmethyl)-2(3H)-furanone (16) Pale yellow liquid. Yield:
18.38%. 1H NMR: {CDCl3, 400 MHz, d (ppm)} 0.89–0.97
(m, 6H), 1.62–1.67 (m, 4H), 1.88–1.94 (m, 1H), 2.07–2.12
(m, 1H), 2.60–2.78 (m, 6H), 2.88–2.90 (m, 4H), 4.57–4.64
(m, 1H), 6.83–6.88 (m, 1H), 6.93–6.95 (m, 1H), 7.05–7.09
(m, 1H), 7.14–7.17 (m, 1H). LC–MS (ESI) (m/z) 333.3
(M ? H)?. HPLC analysis: [95% purity using two dif-
ferent mobile phases.
3,3-Diethyl-4,5-dihydro-5-(4-[4-phenyl]piperazinylmethyl)-
2(3H)-furanone (11) Pale yellow solid. Yield: 22.02%.
1H NMR: {CDCl3, 400 MHz, d (ppm)} 0.89–0.98 (m, 6H),
1.60–1.66 (m, 4H), 1.90–1.96 (m, 1H), 2.06–2.11 (m, 1H),
2.58–2.80 (m, 6H), 3.14–3.21 (m, 4H), 4.57–4.63 (m, 1H),
6.85 (t, 1H), 6.92 (d, 2H), 7.26 (t, 2H). Elemental analysis:
calcd for: C19H28N2O2: C, 72.12; H, 8.92; N, 8.85. Found:
C, 72.40; H, 9.13; N, 8.65%.
3,3-Diethyl-4,5-dihydro-5-(2-[4-piperidinyl]benzimidazo-
lylmethyl)-2(3H)-furanone (17) Pale yellow solid. Yield:
10.15%. 1H NMR: {CDCl3, 400 MHz, d (ppm)} 0.85–0.96
(m, 6H), 1.57–1.65 (m, 4H), 1.86–2.28 (m, 9H), 2.51–2.64
(m, 2H), 2.88–3.09 (m, 3H), 4.52–4.58 (m, 1H), 7.15–7.25
(m, 2H), 7.51–7.54 (m, 2H). LC–MS (ESI) (m/z) 356.0
(M ? H)?. HPLC analysis: [95% purity using two dif-
ferent mobile phases.
3,3-Diethyl-4,5-dihydro-5-(4-[2-methoxyphenyl]piperaz-
inylmethyl)-2(3H)-furanone (12) Pale yellow liquid. Yield:
17.04%. 1H NMR: {CDCl3, 400 MHz, d (ppm)} 0.89–0.97
(m, 6H), 1.60–1.65 (m, 4H), 1.88–1.91 (m, 1H), 2.05–2.10
(m, 1H), 2.60–2.81 (m, 6H), 3.08 (m, 4H), 3.85 (s, 3H),
4.58–4.62 (m, 1H), 6.84–7.01 (m, 4H). LC–MS (ESI) (m/
z) 347.3 (M ? H)?. HPLC analysis: [95% purity using
two different mobile phases.
3,3-Diethyl-4,5-dihydro-5-(4-[4-phenyl]piperidinylmeth-
yl)-2(3H)-furanone (18) Pale yellow liquid. Yield:
23.74%. 1H NMR: {CDCl3, 400 MHz, d (ppm)} 0.93–1.01
(m, 6H), 1.63–1.69 (m, 4H), 1.81–1.95 (m, 5H), 2.09–2.14
(m, 1H), 2.23–2.29 (m, 2H), 2.51 (m, 1H), 2.64–2.67 (m,
2H), 3.05 (d, 11.2 Hz, 1H), 3.19 (d, 12.4 Hz, 1H),
4.62–4.63 (m, 1H), 7.22–7.34 (m, 5H). LC–MS (ESI) (m/
z) 316.3 (M ? H)?. HPLC analysis: [95% purity using
two different mobile phases.
(4-Piperidinylphenyl)-1-carbamic acid 3,3-diethyl-4,5-
dihydro-2(3H)-furanone methylester (13) Pale yellow solid.
1
Yield: 52.66%. H NMR: {CDCl3, 400 MHz, d (ppm)}
0.89–0.97 (m, 6H), 1.52–1.72 (m, 10H), 1.90–1.95 (m,
1H), 2.06–2.11 (m, 1H), 3.07–3.10, 4.12–4.16 (m, 1H),
4.38–4.42 (m, 1H), 4.61–4.67 (m, 1H), 6.57 (s, 1H), 6.89
(d, 2H), 7.22–7.23 (m, 2H). LC–MS (ESI) (m/z) 376.2
(M ? H)?. HPLC analysis: [95% purity using two dif-
ferent mobile phases.
3,3-Diethyl-4,5-dihydro-5-(4-[2-cyanophenyl]piperazinylm-
ethyl)-2(3H)-furanone (19) Pale yellow liquid. Yield:
15.80%. 1H NMR: {CDCl3, 400 MHz, d (ppm)} 0.85–0.93
(m, 6H), 1.55–1.61 (m, 4H), 1.84–1.90 (m, 1H), 2.01–2.06
(m, 1H), 2.57–2.80 (m, 6H), 3.14–3.21 (m, 4H), 4.52–4.57
(m, 1H), 6.93–6.97 (m, 2H), 7.41–7.45 (m, 1H), 7.49 (dd, 8
and 4 Hz, 1H). LC–MS (ESI) (m/z) 342.2 (M ? H)?.
HPLC analysis: [95% purity using two different mobile
phases.
3,3-Diethyl-4,5-dihydro-5-(4-[3-methoxyphenyl]piperazi-
nylmethyl)-2(3H)-furanone (14) Pale yellow liquid.
1
Yield: 40.54%. H NMR: {CDCl3, 400 MHz, d (ppm)}
0.87–0.96 (m, 6H), 1.58–1.64 (m, 4H), 1.88–1.93 (m, 1H),
2.03–2.08 (m, 1H), 2.55–2.76 (m, 6H), 3.12–3.18 (m, 4H),
3.76 (s, 3H), 4.56–4.59 (m, 1H), 6.38–6.53 (m, 3H),
7.12–7.16 (t, 1H). LC–MS (ESI) (m/z) 347.3 (M ? H)?.
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