K. A. Agha et al.
(OCO), 153.1 (H2N–C), 137.3 (OCH2C–), 129.1 (Ar–C),
128.6 (Ar–C), 128.4 (Ar–C), 128.3 (Ar–C), 127.5 (Ar–C),
122.5 (Ar–C), 118.8 (Ar–C), 112.0 (Ar–C), 66.5 (OCH2),
44.6 (CH2) ppm.
13C NMR (125 MHz, DMSO-d6): δ = 169.0 (CO), 160.1
[=C–OCH3], 129.0 (Ar–C), 128.1 (Ar–C), 113.7 (Ar–C),
60.3 (OCH3), 55.3 [–N(CH2)2–], 45.8 [HN–(CH2)2–] ppm.
N‑ ( 2 ‑ A m i n o e t h y l ) ‑ 4 ‑ m e t h o x y b e n z a m i d e ( 3 l ,
C10H14N2O2) Yellow microcrystals; yield 1.61 g (83%);
m.p.: 89–91 °C; 1H NMR (500 MHz, CDCl3): δ=7.78 (d,
J=8.5 Hz, 2H, Ar–H), 6.98 (s, 1H, NH), 6.90 (d, J=8.5 Hz,
2H, Ar–H), 3.83 (s, 3H, OCH3), 3.53 (t, J=5.5 Hz, 2H, –
CONHCH2), 2.98 (t, J=5.3 Hz, 2H, –CH2NH2), 1.25 (s, 2H,
NH2) ppm; 13C NMR (125 MHz, CDCl3): δ=167.3 (C=O),
162.0 (C–OCH3), 128.7 (Ar–C), 126.5 (Ar–C), 113.6 (Ar–
C), 55.3 (OCH3), 40.9 (CH2NH2), 29.6 (CONHCH2) ppm.
Benzyl [2‑oxo‑2‑(piperazin‑1‑yl)ethyl]carbamate (3g,
1
C14H19N3O3) Oil; yield 2.3 g (83%); H NMR (500 MHz,
DMSO-d6): δ = 7.35–7.27 (m, 6H, Ar–H, –CO–NH–),
5.02 (s, 2H, OCH2), 3.83 (s, 2H, CH2CO), 3.32 [d, br, 4H,
CON(CH2–)2–], 2.62 [d, br, 4H, HN(CH2)2–], 1.67 (s, 1H,
NH) ppm; 13C NMR (125 MHz, DMSO-d6): δ=167.1 (CO),
156.6 (OCO), 137.2 (OCH2C), 128.5 (Ar–C), 127.9 (Ar–C),
127.8 (Ar–C), 65.5 (OCH2), 45.8 [CON(CH2–)2–], 45.5
[HN(CH2)2–], 42.1 (COCH2) ppm.
N‑(4‑Aminophenyl)‑3,4,5‑trimethoxybenzamide (3m,
C16H18N2O4) Gray microcrystals; yield 1.39 g (92%); m.p.:
Benzyl [2‑[(2‑aminoethyl)amino]‑2‑oxoethyl]carbamate (3h,
C12H17N3O3) Buf microcrystals; yield 2.14 g (85%); m.p.:
131–133 °C; 1H NMR (500 MHz, DMSO-d6): δ=7.92 (s,
1H, OCONH), 7.41 (s, 1H, NH), 7.34–7.27 (m, 5H, Ar–H),
4.99 (s, 2H, OCH2), 3.54 (s, 2H, COCH2), 3.04 (t, J=5.5 Hz,
2H, NHCH2), 2.53 (t, J=5.5 Hz, 2H, NHCH2CH2), 1.71(s,
2H, NH2) ppm; 13C NMR (125 MHz, DMSO-d6): δ=169.1
(NHCOCH2), 156.5 (OCO), 137.1 (Ar–C), 128.4 (Ar–C),
127.8 (Ar–C), 127.7 (Ar–C), 65.5 (OCH2), 43.6 (COCH2),
41.0 (CONHCH2), 38.3 (CH2NH2) ppm.
1
204–206 °C; H NMR (500 MHz, DMSO-d6): δ = 9.77
(s, 1H, NH), 7.31 (d, J = 8.5 Hz, 2H, Ar–H), 7.24 (s, 2H,
Ar–H), 6.55 (d, J=8.5 Hz, 2H, Ar–H), 4.95 (s, 2H, NH2),
3.85 (s, 6H, 2m-(OCH3)), 3.71 (s, 3H, p-(OCH3)) ppm; 13
C
NMR (125 MHz, DMSO-d6): δ=164.1 (C=O), 152.6 (C-m-
(OCH3), 145.4 (C–NH2), 139.9 (C-p-(OCH3), 130.4 (Ar–C),
127.9 (Ar–C), 122.7 (Ar–C), 113.7 (Ar–C), 105.0 (Ar–C),
60.1 (p-OCH3), 56.0 (m-OCH3) ppm.
N‑ ( 4 ‑ A m i n o p h e n y l ) ‑ 3 ‑ n i t r o b e n z a m i d e ( 3 n ,
C13H11N3O3) Orange microcrystals; yield 1.14 g (89%); m.p.:
221–223 °C; 1H NMR (500 MHz, DMSO-d6): δ=10.23 (s,
1H, NH), 8.75 (s, 1H, Ar–H), 8.40 (d, J=8.0 Hz, 1H, Ar–H),
8.36 (d, J = 8.0 Hz, 1H, Ar–H), 7.80 (t, J = 7.8 Hz, 1H,
Ar–H), 7.38 (d, J=8.5 Hz, 2H, Ar–H), 6.55 (d, J=8.5 Hz,
2H, Ar–H), 5.00 (s, 2H, NH2) ppm; 13C NMR (125 MHz,
DMSO-d6): δ=156.5 (C=O), 152.4 (=C–NO2), 143.1 (=C–
NH2), 137.0 (=C–CO–), 134.3 (Ar–C), 128.4 (Ar–C), 127.9
(Ar–C), 127.8 (Ar–C), 121.8 (Ar–C), 121.1 (Ar–C), 118.4
(Ar–C) ppm.
N‑ ( 4 ‑ A m i n o p h e ny l ) ‑ 4 ‑ m e t h ox y b e n z a m i d e (3 i ,
C14H14N2O2) Buf microcrystals; yield 1.1 g (91%); m.p.:
169–171 °C;1H NMR (500 MHz, DMSO-d6): δ = 9.71
(s, 1H, NH), 7.90 (d, J = 8.7 Hz, 2H, Ar–H), 7.34 (d,
J=8.5 Hz, 2H, Ar–H), 7.02 (d, J=8.7 Hz, 2H, Ar–H), 6.52
(d, J=8.5 Hz, 2H, Ar–H), 4.90 (s, 2H, NH2), 3.82 (s, 3H,
OCH3) ppm; 13C NMR (125 MHz, DMSO-d6): δ = 164.1
(C=O), 161.5 (C–OCH3), 145.1 (C–NH2), 129.3 (Ar–C),
128.3 (Ar–C), 127.4 (Ar–C), 122.3 (Ar–C), 113.7 (Ar–C),
113.5 (Ar–C), 55.4 (OCH3) ppm.
N‑ ( 2 ‑ A m i n o p h e ny l ) ‑ 4 ‑ m e t h ox y b e n z a m i d e ( 3 j ,
C14H14N2O2) Buff microcrystals; yield 1 g (83%); m.p.:
135–137 °C; 1H NMR (500 MHz, DMSO-d6): δ=9.55 (s,
1H, NH), 7.97 (d, J=7.5 Hz, 2H, Ar–H), 7.15-6.96 (m, 4H,
Ar–H), 6.77 (d, J=7.5 Hz, 2H, Ar–H), 4.87 (s, 2H, NH2),
3.83 (s, 3H, OCH3) ppm; 13C NMR (125 MHz, DMSO-d6):
δ=173.2 (CO), 167.6 (=C–OCH3), 158.9 (=C–NH2), 128.9
(Ar–C), 127.2(Ar–C), 123.6 (Ar–C), 121.0 (Ar–C), 118.8
(Ar–C), 118.4 (Ar–C), 117.2 (Ar–C), 116.0 (Ar–C), 53.5
(OCH3) ppm.
(3‑Nitrophenyl)(piperazin‑1‑yl)methanone (3o,
C11H13N3O3) Yellow microcrystals; yield 1.92 g (82%);
m.p.: 64–66 °C; 1H NMR (500 MHz, DMSO-d6): δ=8.65
(s, 1H, Ar–H), 8.36 (d, J = 9.0 Hz, 1H, Ar–H), 8.19 (d,
J=7.5 Hz, 1H, Ar–H), 7.65 (t, J=7.7 Hz, 1H, Ar–H), 3.54
[t, J=5.7 Hz, 4H, CON(CH2–)2–], 3.00 [t, J=5.7 Hz,, 4H,
HN(CH2)2–], 0.87 (s, 1H, NH) ppm; 13C NMR (125 MHz,
DMSO-d6): δ=164.2 (C=O), 147.8 (C–NO2), 136.0 (Ar–
C), 133.8 (Ar–C), 130.1(Ar–C), 125.8 (Ar–C), 122.0 (Ar–
C), 43.02 [CON(CH2–)2–], 41.0 [HN(CH2)2–] ppm.
(4‑Methoxyphenyl)(piperazin‑1‑yl)methanone (3k,
C
DMSO-d6): δ = 7.32 (d, J = 8.3 Hz, 2H, Ar–H), 6.96 (d,
J=8.3 Hz, 2H, Ar–H), 3.77 (s, 3H, OCH3), 3.29 [br s, 4H,
–CON(CH2)2–], 2.65 [br s, 4H, –CON(CH2)2(CH2)2–] ppm;
N‑(4‑Aminophenyl)stearamide (3p, C24H42N2O) White
1
12H16N2O2) Oil; yield 1.74 g (79%); 1H NMR (500 MHz,
microcrystals; yield 1.76 g (94%); m.p.: 117–119 °C; H
NMR (500 MHz, DMSO-d6): δ = 9.39 (s, 1H, NH), 7.18
(d, J=8.5 Hz, 2H, Ar–H), 6.46 (d, J=8.5 Hz, 2H, Ar–H),
4.80 (s, 2H, NH2), 2.18 (t, J = 7.5 Hz, 2H, –CH2–CO–),
1 3