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4.1.32. 1-Acetyl-N-(3-chlorophenyl)-N-(3-(4-(4-
4.1.38. 1-Acetyl-N-(3-chlorophenyl)-N-(3-(4-(4-
fluorophenethylcarbamoyl)piperidin-1-yl)propyl)piperidine-4-
carboxamide (16n)
fluorobenzylcarbamoyl)piperidin-1-yl)propyl)piperidine-4-
carboxamide (16h)
Yellow solid (43%); mp: 75e78 ꢁC. 1H NMR (CDCl3, 500 MHz)
d:
White solid (44%); mp: 66e68 ꢁC. 1H NMR (CDCl3, 500 MHz)
d:
7.44e7.41 (m, 2H, AreH), 7.25e7.19 (m, 4H, AreH), 7.03e6.99 (m, 2H,
AreH), 4.51 (d, J ¼ 13.5 Hz,1H), 4.38 (d, J ¼ 6.0 Hz, 2H), 3.78e3.66 (m,
4H), 3.22e3.10 (m, 2H), 2.86e2.81 (m, 1H), 2.67e2.63 (m, 1H), 2.62
(s, 2H, CH2), 2.45e2.30 (m, 5H), 2.18e2.10 (m, 2H), 2.05 (s, 3H, CH3),
1.92e1.60 (m, 6H). HRMS (ESIþ) m/z calculated for C30H39ClFN4O3
[M þ H]þ, 557.2695; found, 557.2705.
7.36e7.35 (m, 2H, AreH), 7.16 (s,1H, AreH), 7.10e7.03 (m, 3H, AreH),
6.96e6.92 (m, 2H, AreH), 5.65 (brs, 1H), 4.48 (d, J ¼ 13.5 Hz, 1H),
3.74e3.71 (d, J ¼ 13.5 Hz,1H), 3.64e3.61 (m, 2H), 3.45e3.41 (m, 2H),
2.83e2.72 (m, 5H), 2.31e2.24 (m, 4H), 2.00 (s, 3H, CH3), 1.98e1.94
(m, 1H), 1.87e1.82 (m, 2H), 1.76e1.56 (m, 10H). 13C NMR (CDCl3,
100 MHz) d: 174.77, 173.65, 168.64, 162.47, 160.53, 143.47, 135.25,
134.48, 130.78, 130.07, 128.46, 128.21, 126.33, 55.67, 53.08, 47.97,
45.40, 43.14, 40.55, 39.34, 34.75, 28.75, 28.20, 25.14, 21.25. HRMS
(ESIþ) m/z calculated for C31H40ClFN4O3 [M þ H]þ571.2851; found,
571.2860.
4.1.33. 1-Acetyl-N-(3-(4-(4-chlorobenzylcarbamoyl)piperidin-1-yl)
propyl)-N-(3-chlorophenyl)piperidine-4-carboxamide (16i)
Brown solid (45%); mp: 46e49 ꢁC. 1H NMR (500 MHz, CDCl3)
d
: 7.38e7.37 (m, 2H, AreH), 7.27e7.26 (m, 2H, AreH), 7.18e7.15
4.1.39. 1-Acetyl-N-(3-(4-(4-chlorophenethylcarbamoyl)piperidin-
(m, 3H, AreH), 7.07e7.06 (m, 1H, AreH), 5.99 (brs, 1H), 4.99 (d,
J ¼ 13.5 Hz, 1H), 4.37 (d, J ¼ 6 Hz, 2H), 3.75 (d, J ¼ 13.5 Hz, 1H),
3.67 (t, J ¼ 7.5 Hz, 2H), 2.91e2.79 (m, 3H), 2.32 (brs, 4H), 2.14e
2.09 (m, 1H), 2.01 (s, 3H, CH3), 1.95e1.94 (m, 2H), 1.85e1.83 (m,
1-yl)propyl)-N-(3-chlorophenyl)piperidine-4-carboxamide (16o)
Yellow solid (49%); mp: 58e60 ꢁC. 1H NMR (CDCl3, 500 MHz)
d:
7.36e7.35 (m, 2H, AreH), 7.23e7.21 (d, J ¼ 8 Hz, 2H, AreH), 7.16 (s,
1H, AreH), 7.07e7.03 (m, 3H, AreH), 5.71 (brs, 1H), 4.45 (d,
J ¼ 10 Hz, 1H), 3.74e3.61 (m, 3H), 3.45e3.41 (m, 2H), 2.84e2.72
(m, 5H), 2.33e2.24 (m, 4H), 2.00 (s, 3H, CH3), 1.98e1.94 (m, 1H),
2H), 1.76e1.55 (m, 8H). 13C NMR (100 MHz, CDCl3)
d 174.71,
173.82, 168.75, 143.55, 137.00, 135.40, 133.24, 130.91, 129.03,
128.81, 128.60, 128.32, 126.45, 55.70, 53.04, 48.02, 45.51, 42.69,
40.66, 39.46, 28.83, 28.32, 25.15, 21.36. HRMS (ESIþ) m/z
calculated for
573.2406.
1.87e1.83 (m, 2H), 1.72e1.54 (m, 10H). 13C NMR (CDCl3, 100 MHz)
d:
174.83, 173.66, 168.68, 143.43, 137.30, 135.26, 132.24, 130.79, 130.00,
128.57, 128.48, 128.20, 126.32, 55.65, 53.06, 47.97, 45.41, 43.13,
40.56, 39.34, 34.91, 28.71, 28.20, 25.11, 21.25. HRMS (ESIþ) m/z
calculated for C31H40Cl2N4O3 [M þ H]þ587.2555; found, 587.2561.
C
30H39Cl2N4O3 [M
þ
H]þ, 573.2399; found,
4.1.34. 1-Acetyl-N-(3-chlorophenyl)-N-(3-(4-(4-
cyanobenzylcarbamoyl)piperidin-1-yl)propyl)piperidine-4-
carboxamide (16j)
4.1.40. 1-Acetyl-N-(3-chlorophenyl)-N-(3-(4-(ethyl(phenethyl)
carbamoyl)piperidin-1-yl)propyl)piperidine-4-carboxamide (16p)
Yellow oil (35%); 1H NMR (CDCl3, 500 MHz)
d: 7.63e7.30 (m,
Yellow oil (32%). 1H NMR (CDCl3, 500 MHz)
d: 7.44e7.28 (m, 4H,
8H, AreH), 4.53e4.45 (m, 3H), 3.80e3.48 (m, 5H), 3.33e3.29 (m,
1H), 3.12e3.08 (m, 1H), 2.97e2.82 (m, 2H), 2.40e2.07 (m, 7H),
2.05 (s, 3H, CH3), 1.98e1.63 (m, 7H). HRMS (ESIþ) m/z calculated
for C31H39ClN5O3 [M þ H]þ, 564.2741; found, 564.2752.
AreH), 7.25e7.14 (m, 5H, AreH), 4.56e4.53 (m, 1H), 3.80e3.62 (m,
4H), 3.56e3.41 (m, 3H), 3.20e3.11 (m, 3H), 2.86e2.80 (m, 3H),
2.78e2.61 (m, 2H), 2.40e2.25 (m, 4H), 2.20e2.06 (m, 4H), 2.07 (s,
3H, CH3),1.96e1.62 (m, 6H),1.16e1.08 (m, 3H, CH3). HRMS (ESIþ) m/
z calculated for C33H46ClN4O3 [M þ H]þ581.3258; found, 581.3266.
4.1.35. 1-Aacetyl-N-(3-chlorophenyl)-N-(3-(4-(phenylcarbamoyl)
piperidin-1-yl)propyl)piperidine-4-carboxamide (16k)
4.1.41. 1-Acetyl-N-(3-chlorophenyl)-N-(3-(4-(ethyl(4-
fluorophenethyl)carbamoyl)piperidin-1-yl)propyl)piperidine-4-
carboxamide (16q)
Yellow solid (34%); mp: 92e95 ꢁC. 1H NMR (CDCl3, 500 MHz)
d
: 7.54e7.40 (m, 5H, AreH), 7.34e7.31 (m, 2H, AreH), 7.12e7.09
White oil (42%). 1H NMR (CDCl3, 500 MHz)
d: 7.34e7.33 (m, 2H,
(m, 2H, AreH), 4.52 (d, J ¼ 13.5 Hz, 1H), 3.76 (d, J ¼ 13.5 Hz, 1H),
3.71e3.68 (m, 2H), 3.04 (d, J ¼ 10.5 Hz, 2H), 2.87e2.82 (m, 1H),
2.45e2.10 (m, 13H), 2.06 (s, 3H, CH3), 2.00e1.94 (m, 4H). HRMS
(ESIþ) m/z calculated for C29H38ClN4O3 [M þ H]þ525.2632; found,
525.2637.
AreH), 7.16e7.15 (m,1H, AreH), 7.11e7.04 (m, 3H, AreH), 6.96e6.88
(m, 2H, AreH), 4.47 (d, J ¼ 12 Hz, 1H), 3.72e3.70 (d, J ¼ 12 Hz, 1H),
3.63e3.62 (m, 2H), 3.43e3.40 (m, 2H), 3.34e3.30 (m, 1H), 3.14e3.11
(m, 1H), 2.86e2.74 (m, 5H), 2.29e2.21 (m, 5H), 1.99 (s, 3H, CH3),
1.89e1.85 (m, 1H), 1.81e1.55 (m, 10H), 1.34e1.32 (m, 1H), 1.08e1.04
(m, 3H). 13C NMR (CDCl3, 100 MHz)
d: 174.62, 173.72, 168.69, 143.57,
4.1.36. 1-Acetyl-N-(3-chlorophenyl)-N-(3-(4-(ethyl(phenyl)
carbamoyl)piperidin-1-yl)propyl)piperidine-4-carboxamide (16l)
Yellow solid (33%); mp: 70e72 ꢁC. 1H NMR (CDCl3, 500 MHz)
135.28, 134.96, 130.82, 130.27, 130.16, 128.48, 128.26, 127.77, 126.40,
55.82, 53.21, 48.08, 45.46, 42.75, 40.61, 39.41, 34.96, 33.27, 28.78,
28.26, 25.17, 21.30, 14.73, 12.87. HRMS (ESIþ) m/z calculated for
d
: 7.40e7.26 (m, 5H, AreH), 7.11e7.00 (m, 4H, AreH), 4.43 (d,
C
33H44ClFN4O3 [M þ H]þ599.3164; found, 599.3156.
J ¼ 12.5 Hz, 1H), 4.16e4.03 (m, 1H), 3.70e3.50 (m, 5H), 2.95e
2.66 (m, 4H), 2.50e2.05 (m, 10H), 1.97 (s, 3H, CH3), 1.92e1.73 (m,
5H), 1.00 (t, J ¼ 7.0 Hz, 3H, CH3). HRMS (ESIþ) m/z calculated for
4.1.42. 1-Acetyl-N-(3-(4-((4-chlorophenethyl)(ethyl)carbamoyl)
piperidin-1-yl)propyl)-N-(3-chlorophenyl)piperidine-4-
carboxamide (16r)
C
31H42ClN4O3 [M þ H]þ553.2945; found, 553.2952.
Yellow oil (48%). 1H NMR (CDCl3, 500 MHz)
d: 7.36 (brs, 2H, Are
4.1.37. 1-Acetyl-N-(3-chlorophenyl)-N-(3-(4-(phenethylcarbamoyl)
piperidin-1-yl)propyl)piperidine-4-carboxamide (16m)
H), 7.26e7.25 (m, 1H, AreH), 7.22e7.17 (m, 2H, AreH), 7.11e7.05 (m,
3H, AreH), 4.50 (d, J ¼ 13.5 Hz, 1H), 3.75e3.73 (d, J ¼ 13.5 Hz, 1H),
3.67e3.62 (m, 2H), 3.46e3.41 (m, 2H), 3.36e3.32 (m, 1H), 3.16e3.11
(m, 1H), 2.89e2.76 (m, 5H), 2.35e2.24 (m, 5H), 2.02 (s, 3H, CH3),
1.92e1.88 (m, 1H), 1.84e1.58 (m, 10H), 1.37e1.35 (m, 1H), 1.10e1.06
Yellow solid (46%); mp: 82e85 ꢁC. 1H NMR (CDCl3, 500 MHz)
d:
7.44e7.29 (m, 4H, AreH), 7.25e7.14 (m, 5H, AreH), 4.51 (d,
J ¼ 13.0 Hz, 1H), 3.83e3.65 (m, 5H), 3.56e3.47 (m, 2H), 3.19e3.05
(m, 2H), 2.90e2.77 (m, 4H), 2.72e2.60 (m, 2H), 2.40e2.28 (m, 4H),
2.05 (s, 3H, CH3), 1.95e1.65 (m, 8H). HRMS (ESIþ) m/z calculated for
(m, 3H). 13C NMR (CDCl3, 100 MHz)
d: 174.61, 173.67, 168.64, 143.43,
137.74, 135.24, 131.91, 130.78, 130.14, 128.78, 128.39, 128.21, 126.36,
55.77, 53.14, 48.03, 45.42, 42.75, 40.57, 39.36, 35.12, 33.41, 28.74,
C
31H42ClN4O3 [M þ H]þ553.2945; found, 553.2950.