654
A. Ranise et al. / Il Farmaco 56 (2001) 647–657
356.85, yield 77%, m.p. 107–109 °C (diethyl ether–
petroleum ether 60–80 °C 2:1). H NMR (CDCl3): l
0.88 (d, J=5 Hz, 3H, CH3/pip) 0.90–1.98 (m, 5H,
2CH2+CH/pip), 2.23–3.08 (m, 2H, CH2N/pip), 3.68–
4.38 (m, 2H, CH2N/pip), 7.08–7.80 (m, 9H, arom. H).
(d, J=6 Hz, 3H, CH3/pip), 1.05–1.92 (m, 5H, 2CH2+
CH/pip), 2.50–3.13 (m, 2H, CH2N/pip), 3.38–4.48 (m,
2H, CH2N/pip), 6.67–7.90 (m, 9H, arom. H).
1
4f:
N-(4-Chloro)benzoyl-N-phenyl-4-methylpipe-
ridine-1-carboxamide. Formula C20H21N2O2Cl, MM
1
3g:
N-(2-Furane)carbonyl-N-phenyl-3-methylpipe-
356.85, yield 75%, m.p. 113–115 °C (diethyl ether). H
ridine-1-carboxamide. Formula C18H20N2O3, MM
NMR (CDCl3): l 0.88 (d, J=6 Hz, 3H, CH3/pip),
1.05–1.88 (m, 5H, 2CH2+CH/pip), 2.50–3.15 (m, 2H,
CH2N/pip), 3.80–4.15 (m, 2H, CH2N/pip), 7.05–7.80
(m, 9H, arom. H).4g: N-(2-Furane)carbonyl-N-phenyl-
4-methylpiperidine-1-carboxamide. Formula C18H20N2-
O3, MM 312.37, yield 90%, m.p. 118–119 °C (dichloro-
312.37, yield 79%, m.p.132–133 °C (dichloromethane–
1
diethyl ether 1:8). H NMR (CDCl3): l 0.88 (d, J=5
Hz, 3H, CH3/pip) 0.90–2.00 (m, 5H, 2CH2+CH/pip),
2.17–3.16 (m, 2H, CH2N/pip), 3.84–4.44 (m, 2H,
CH2N/pip), 6.44–6.62 (m, 1H, H-4 fur.), 6.95 (d, J=4
Hz, 1H, H-3 fur.), 7.13–7.69 (m, 6H, 5 arom. H and
H-5 fur.).
1
methane–diethyl ether 1:9). H NMR (CDC13): l 0.88
(d, J=6 Hz, 3H, CH3/pip), 1.03–1.90 (m, 5H, 2CH2+
CH/pip), 2.27–3.20 (m, 2H, CH2N/pip), 3.95–4.50 (m,
2H, CH2N/pip), 6.40–6.60 (m, 1H, H-4 fur.), 6.68–7.19
(d, J=4 Hz, 1H, H-3 fur.) 7.03–7.70 (m, 6H, 5 arom.
H and H-5 fur.).
3h:
N-(2-Thiophene)carbonyl-N-phenyl-3-methyl-
piperidine-1-carboxamide. Formula C18H20N2O2S, MM
328.43, yield 83%, m.p. 113–114 °C (diethyl ether–
1
petroleum ether 60–80 °C 2:1). H NMR (CDCl3): l
0.88 (d, J=5 Hz, 3H, CH3/pip) 0.90–2.05 (m, 5H,
2CH2+CH/pip), 2.33–3.20 (m, 2H, CH2N/pip), 3.87–
4.45 (m, 2H, CH2N/pip), 6.85–7.15 and 7.25–7.68 (m,
8H, 5 arom. H and 3H thioph.).
4h:
N-(2-Thiophene)carbonyl-N-phenyl-4-methyl-
piperidine-1-carboxamide. Formula C18H20N2O2S, MM
328.43, yield 85%, m.p. 109–111 °C (diethyl ether). H
1
NMR (CDCl3): l 0.85 (d, J=6 Hz, 3H, CH3/pip),
1.05–1.95 (m, 5H, 2CH2+CH/pip), 2.60–3.20 (m, 2H,
CH2N/pip), 3.98–4.50 (m, 2H, CH2N/pip), 6.88–7.03
and 7.21–7.64 (m, 8H, 5 arom. H and 3H tioph.).
5a: N-[2-(4-Chlorophenoxy)-2-methyl]propionyl-N-
phenyl-4-phenylpiperidine-1-carboxamide.
C28H29N2O3C1, MM 477.00, yield 65%, m.p. 159–
160 °C (dichloromethane–diethyl ether 1:7). H NMR
4a: N-[2-(4-Chlorophenoxy)-2-methyl]propionyl-N-
phenyl-4-methylpiperidine-1-carboxamide.
Formula
C23H27N2O3C1, MM 414.93, yield 72%, m.p. 120–
121 °C (diethyl ether–petroleum ether 60–80 °C 2:1).
1H NMR (CDCl3): l 0.77 (d, J=6 Hz, 3H, CH3/pip),
1.09–1.50 (m, 5H, 2CH2+CH/pip), 1.64 (s, 6H,
2CH3C), 2.27–2.98 (m, 2H, CH2N/pip), 3.10–4.40 (m,
2H, CH2N/pip), 6.87–7.64 (m, 9H, arom. H).
Formula
1
(CDCl3): l 1.01–1.90 (m, 4H, 2CH2/pip), 1.66 (s, 6H,
2CH3C), 2.03–2.96 (m, 3H, CH2N and CH/pip), 3.71–
4.70 (m, 2H, CH2N/pip), 6.50–7.93 (m, 14H, arom. H).
4b:
N-Benzoyl-N-phenyl-4-methylpiperidine-1-car-
boxamide. Formula C20H22N2O2, MM 322.41, yield
81%, m.p. 90–92 °C (diethyl ether–petroleum ether
60–80 °C 2:1). H NMR (CDCl3): l 0.87 (d, J=6 Hz,
3H, CH3/pip), 1.09–1.87 (m, 5H, 2CH2+CH/pip),
2.52–3.14 (m, 2H, CH2N/pip), 3.90–4.15 (m, 2H,
CH2N/pip), 6.80–7.92 (m, 10H, arom. H).
5b:
N-Benzoyl-N-phenyl-4-phenylpiperidine-1-car-
1
boxamide. Formula C25H24N2O2, MM 384.48, yield
76%, m.p. 166–167 °C (diethyl ether). 1H NMR
(CDCl3): l 1.00–2.07 (m, 4H, 2CH2/pip), 2.40–3.27 (m,
3H, CH2N and CH/pip), 4.13–4.65 (m, 2H, CH2N/
pip), 6.80–7.98 (m, 15H, arom. H).
4c:
N-(4-Methyl)benzoyl-N-phenyl-4-methylpipe-
ridine-1-carboxamide. Formula C21H24N2O2, MM
5c:
N-(4-Methyl)benzoyl-N-pheny1-4-phenylpipe-
336.43, yield 92%, m.p. 122–123 °C (diethyl ether–
petroleum ether 60–80 °C 2:1). H NMR (CDCl3): l
ridine-1-carboxamide. Formula C26H26N2O2, MM
398.50, yield 75%, m.p. 139–140 °C (diethyl ether). H
1
1
0.87 (d, J=6 Hz, 3H, CH3/pip), 1.1–1.85 (m, 5H,
2CH2+CH/pip), 2.35 (s, 3H, CH3/tolyl), 2.50–3.10 (m,
2H, CH2N/pip), 3.90–4.45 (m, 2H, CH2N/pip), 6.75–
7.27 (m, 9H, arom. H).
NMR (CDC13): l 1.00–2.08 (m, 4H, 2CH2/pip), 2.45–
3.26 (m, 3H, CH2N and CH/pip), 4.08–4.66 (m, 2H,
CH2N/pip), 6.68–7.88 (m, 14H, arom. H).
5d: N-(4-Methoxy)benzoyl-N-phenyl-4-phenylpipe-
ridine-1-carboxamide. Formula C26H26N2O3, MM
414.50, yield 71%, m.p. 114–116 °C (diethyl ether–
4d: N-(4-Methoxy)benzoyl-N-phenyl-4-methylpipe-
ridine-1-carboxamide. Formula C21H24N2O3, MM
1
1
352.43, yield 70%, m.p. 102–103 °C (diethyl ether). H
petroleum ether 60–80 °C 9:1). H NMR (CDCl3): l
NMR (CDCl3): l 0.89 (d, J=6 Hz, 3H, CH3/pip),
1.07–1.93 (m, 5H, 2CH2+CH/pip), 2.50–3.15 (m, 2H,
CH2N/pip), 3.80 (s, 3H, CH3O), 3.90–4.25 (m, 2H,
CH2N/pip), 6.70–7.90 (m, 9H, arom. H).
1.04–2.03 (m, 4H, 2CH2/pip), 2.38–3.34 (m, 3H, CH2N
and CH/pip), 3.85 (s, 3H, CH3O), 4.13–4.68 (m, 2H,
CH2N/pip), 6.70–7.97 (m, 14H, arom. H).
5e:
N-(4-Fluoro)benzoyl-N-phenyl-4-phenylpipe-
4e:
N-(4-Fluoro)benzoyl-N-phenyl-4-methylpipe-
ridine-1-carboxamide. Formula C25H23N2O2F, MM
ridine-1-carboxamide. Formula C20H21N2O2F, MM
402.47, yield 75%, m.p. 163–164 °C (dichloro-
methane–diethyl ether 1:7). H NMR (CDCl3): l 1.00–
2.07 (m, 4H, 2CH2/pip), 2.35–3.27 (m, 3H, CH2N and
1
340.40, yield 76%, m.p. 130–131 °C (dichloro-
1
methane–diethyl ether 1:9). H NMR (CDCl3): l 0.87