Med Chem Res
1704, 1587, 1527, 1454, 1319, 1282, 1167, 1116; ES-MS
(m/z) [M + H]+: 315; Anal. Calcd for C16H21F3N2O.HCl:
C, 54.78; H, 6.32; N, 7.99. Found: C, 54.66; H, 6.54; N,
7.90.
(1H, m, 3-CH), 3.39 (3H, s, 3‘-OCH3), 3.42 (2H, m, 2‘-
CH2O), 3.47 (1H, m, 1‘-NCH), 3.73 (1H, m, 1‘-NCH), 3.80
(1H, m, 6-CHN), 3.88 (1H, m, 6-CHN), 4.16 (1H, m, 2-
COCHN), 7.44 (1H, m, ArH), 7.54 (1H, m, ArH), 7.79 (1H,
m, ArH), 8.10 (1H, m, ArH). 1.18 (3H, m, 4‘-CH3),
1.67–1.97 (5H, m, 3-CH, 4-CH2, 5-CH2), 2.33 (1H, m, 3-
CH), 3.35–3.58 (5H, m, 2‘-CH2O, 3‘-OCH2, 1‘-NCH), 3.75
(2H, m, 1‘-NCH, 6-CHN), 3.87 (1H, m, 6-CHN), 4.12 (1H,
m, 2-COCHN), 7.43 (1H, m, ArH), 7.54 (1H, m, ArH), 7.78
(1H, m, ArH), 8.10 (1H, m, ArH);νmax (KBr, cm−1) 3473,
1694, 1619, 1568, 1453, 1334, 1166, 1124, 1070; ES-MS
(m/z) [M + H]+: 331; Anal. Calcd for C16H21F3N2O2: C,
58.17; H, 6.41; N, 8.48. Found: C, 57.99; H, 6.32; N, 8.43.
1- butyl -N-[2-(trifluoromethyl) phenyl]-2-
piperidinecarboxamide Hydrochloride (4k)
Yield 80.0%; mp 220–223 °C; 1H-NMR (500 MHz,
CD3OD) δ 0.96 (3H, t, J = 7.5 Hz, 4‘-CH3), 1.38 (2H, t, J
= 7.2 Hz, 3‘-CH2), 1.67–1.87 (7H, m, 3-CH, 4-CH2, 5-
CH2,2‘-CH2), 2.26 (1H, m, 3-CH), 3.02 (2H, m, 1‘-NCH2),
3.04 (1H, s, 6-CHN), 3.57 (1H, s, 6-CHN), 3.96 (1H, m, 2-
COCHN), 7.49 (1H, m, ArH), 7.60 (1H, m, ArH), 7.74 (3H,
m, ArH);νmax (KBr, cm−1) 2956, 2628, 1687, 1534, 1454,
1320, 1281, 1167, 1109; ES-MS (m/z) [M + H]+: 329;
Anal. Calcd for C17H23F3N2O.HCl %: C, 55.97; H, 6.63; N,
7.68. Found: C, 56.2; H, 6.88; N, 7.73.
1-ethoxyethyl-N-[3-(trifluoromethyl) phenyl]-2-
piperidinecarboxamide hydro-chloride (4o)
Yield 62.2%; mp 143–146 °C; 1H-NMR (500 MHz,
CD3OD) δ 1.18 (3H, m, 4‘-CH3), 1.67–1.97 (5H, m, 3-CH,
4-CH2, 5-CH2), 2.33 (1H, m, 3-CH), 3.35–3.58 (5H, m,2‘-
CH2O, 3‘-OCH2,1‘-NCH), 3.75 (2H, m, 1‘-NCH, 6-CHN),
3.87 (1H, m, 6-CHN), 4.12 (1H, m, 2-COCHN), 7.43 (1H,
m, ArH), 7.54 (1H, m, ArH), 7.78 (1H, m, ArH), 8.10 (1H,
m, ArH);νmax (KBr, cm−1) 3427, 2974, 1694, 1614, 1569,
1451, 1333, 1165, 1122, 1070; ES-MS (m/z) [M + H]+:
345; Anal. Calcd for C16H23F3N2O2: C, 59.29; H, 6.73; N,
8.13. Found: C, 68.99; H, 6.67; N, 8.01.
1-propyl-N-[3 - (trifluoromethyl) phenyl]-2-
piperidinecarboxamide hydrochloride (4l)
Yield 87.7%; mp 166–168 °C; 1H-NMR (500 MHz,
CD3OD) δ 0.92 (3H, t, J = 7.2 Hz, 3‘-CH3), 1.52–1.74 (7H,
m, 3-CH, 4-CH2, 5-CH2, 2‘-CH2), 2.02 (1H, m, 3-CH), 2.06
(1H, m, 1‘-NCH), 2.24 (1H, m, 1‘-NCH), 2.49 (1H, s, 6-
CHN), 2.86 (1H, s, 6-CHN), 3.16 (1H, m, 2-COCHN),7.35
(1H, m, ArH), 7.45 (1H, m, ArH), 7.74 (1H, m, ArH), 7.86
(1H, m, ArH), 8.91 (1H, s, –CONH–);νmax (KBr, cm−1
)
1-propyl-N-[4 - (trifluoromethyl)phenyl]-2-
piperidinecarboxamide hydro- chloride (4p)
3285, 2953, 1678, 1603, 1543, 1446, 1336, 1170, 1122,
1063; ES-MS (m/z) [M + H]+: 315; Anal. Calcd for
C16H21F3N2O.HCl.H2O: C, 52.10; H, 6.72; N, 7.49 Found:
C, 52.10; H, 6.56; N, 7.60.
Yield 79.6%; mp 124–126 °C; 1H-NMR (500 MHz,
CD3OD) δ 0.93 (3H, t, J = 7.5 Hz, 3‘-CH3), 1.54–1.74 (7H,
m, 3-CH, 4-CH2, 5-CH2, 2‘-CH2), 2.04 (1H, m, 3-CH), 2.06
(1H, m, 1‘-NCH), 2.24 (1H, m, 1‘-NCH), 2.50 (1H, s, 6-
CHN), 2.83 (1H, s, 6-CHN), 3.13 (1H, m, 2-COCHN), 7.58
(2H, m, ArH), 7.69 (2H, m, ArH);νmax (KBr, cm−1) 3283,
2945, 1681, 1614, 1527, 1409, 1327, 1159, 1124, 1068; ES-
MS (m/z) [M + H]+: 315; Anal. Calcd for C16H21F3N2O: C,
61.13; H, 6.73; N, 8.91. Found: C, 61.11; H, 6.72; N, 8.74.
1-butyl-N-[3-(trifluoromethyl) phenyl]-2-
piperidinecarboxamide hydrochloride (4m)
Yield 86.4%; mp 149–151 °C; 1H-NMR (500 MHz,
CD3OD) δ 0.96 (3H, t, J = 7.5 Hz, 4‘-CH3), 1.38 (2H, t, m,
3‘-CH2), 1.71–1.97 (7H, m, 3-CH, 4-CH2, 5-CH2, 2‘-CH2),
2.28 (1H, m, 3-CH), 3.09 (2H, m, 1‘-NCH2), 3.15 (1H, s, 6-
CHN), 4.74 (1H, s, 6-CHN),4.06 (1H, m, 2-COCHN), 7.45
(1H, m, ArH), 7.55 (1H, m, ArH), 7.80 (1H, m, ArH), 8.10
(1H, m, ArH);νmax (KBr, cm−1) 3305, 2958, 1678, 1538,
1333, 1170, 1118, 1072; ES-MS (m/z) [M + H]+: 329;
Anal. Calcd for C17H23F3N2O: C, 62.18; H, 7.06; N, 8.53.
Found: C, 62.16; H, 7.32; N, 8.38.
1-butyl-N-[4-(trifluoromethyl) phenyl]-2-
piperidinecarboxamide hydro- chloride (4q)
Yield 67.8%; mp 112–115 °C; 1H-NMR (500 MHz,
CD3OD) δ 0.90 (3H, t, J = 7.5 Hz, 4‘-CH3), 1.34–1.73 (7H,
m, 3-CH, 4-CH2, 5-CH2, 2‘-CH2, 3‘-CH2), 2.06 (1H, m,
3-CH), 2.07 (1H, m, 1‘-NCH), 2.24 (1H, m, 1‘-NCH), 2.56
(1H, s, 6-CHN), 2.83 (1H, s, 6-CHN), 3.14 (1H, m, 2-
COCHN), 7.57 (2H, m, ArH), 7.68 (2H, m, ArH);νmax
(KBr, cm−1) 3289, 2947, 1681, 1614, 1527, 1508, 1409,
1328, 1185, 1124, 1069, 1054; ES-MS (m/z) [M + H]+:
1-methoxyethyl-N-[3-(trifluoromethyl) phenyl]-2-
piperidinecarboxamide hydro- chloride (4n)
Yield 65.2%; mp 169–171 °C; 1H-NMR (500 MHz,
CD3OD) δ 1.67–1.97 (5H, m, 3-CH, 4-CH2, 5-CH2), 2.33