M. Ghaffarzadeh et al.
57 (5). Anal. Calcd for C16H17NO: C, 80.30; H, 7.16; N, 5.85. Found: C,
80.21; H, 7.11; N, 5.78.
N-Benzyl-N-(4-chlorophenyl)propionamide (3d)
White powder; m.p. 112–113ꢀC. IR (KBr): 3011, 2927, 1649, 1580,
828. 1H NMR (500 MHz, CDCl3): d 7.25 (m, 5H, H-Ar), 7.12
(d, J = 2.7Hz, 2H, H-Ar), 6.93 (d, J = 8.1 Hz, 2H, H-Ar), 4.89 (s, 2H,
NCH2), 2.01 (q, J = 7.4Hz, 2H, CH2), 1.10 (t, J = 7.4Hz, 3H, Me).
13C NMR (125 MHz, CDCl3): d 10.2 (Me), 28.4 (CH2-CO), 53.1 (CH2N),
127.9 (CH), 128.8 (CH), 129.2 (CH), 130.1 (CH), 130.2 (CH), 137.6
(Cipso), 141.7 (C-Cl) 142.9 (C-N), 171.5 (CO). MS (E.I.) (70 eV): m/z
(%) 273 (M+, 43), 216 (27), 111 (8), 91 (100), 77 (5). Anal. Calcd for
C16H16ClNO: C, 70.20; H, 5.89; N, 5.12. Found: C, 70.09; H, 5.19;
N, 5.06.
Scheme 1. Model reaction and conditions.
(85), 91 (15), 77 (8), 43 (23). Anal. Calcd for C16H16ClNO: C, 70.20; H,
5.89; N, 5.12. Found: C, 70.28; H, 5.81; N, 5.23.
N-(4-Chlorobenzyl)-N-p-tolylpropionamide (3j)
White powder; m.p. 196-198ꢀC. IR (KBr): 3032, 2935, 1660, 1390,
879, 829. 1H NMR (500 MHz, CDCl3): d 7.26 (d, J = 2.6Hz, 2H, H-Ar),
7.17 (m, 4H, H-Ar), 4.84 (s, 2H, NCH2), 2.17 (s, 3H, Me), 2.01
(q, J = 7.4Hz, 2H, CH2), 1.09 (t, J = 7.4Hz, 3H, Me). 13C NMR
(125 MHz, CDCl3): d 10.4 (Me-CH2), 21.5 (Me-Ar), 28.4 (CH2-CO),
53.0 (CH2N), 127.5 (CH), 128.2 (CH), 129.7 (CH), 130.4 (CH), 133.0
(C-Me), 136.6 (Cipso), 141.9 (C-Cl) 142.5 (C-N)), 172.9 (CO). MS (E.I.)
(70 eV): m/z (%) 287 (M+, 50), 231 (100), 196 (15), 125 (59), 91 (13),
57 (4). Anal. Calcd for C17H18ClNO: C, 70.95; H, 6.30; N, 4.87. Found:
C, 70.82; H, 6.21; N, 4.78.
N-(4-Methoxybenzyl)-N-p-tolylacetamide (3e)
Cream powder; m.p. 102–104ꢀC. IR (KBr): 3064, 2922, 1633, 1521,
814.1H NMR (500 MHz, CDCl3): d 7.14 (d, J = 8.4 Hz, 4H, H-Ar), 6.86
(d, J = 8.1 Hz, 2H, H-Ar), 6.81 (d, J = 8.1 Hz, 2H, H-Ar), 4.82 (s, 2H,
NCH2), 3.81 (s, 3H, OMe), 2.37 (s, 3H, Me), 1.88 (s, 3H, Me).
13C NMR (125 MHz, CDCl3): d 21.5 (Me-Ar), 28.2 (Me-CO), 52.7
(CH2N), 55.6 (OMe), 114.1 (CH), 128.6 (CH), 129.2 (CH), 130.5
(CH), 133.6 (C-Me), 138.1 (Cipso), 140.3 (C-N), 159.2 (C-OMe),
174.2 (CO). MS (E.I.) (70 eV): m/z (%) 269 (M+, 25), 226 (5), 162
(5), 121 (100). Anal. Calcd for C17H19NO2: C, 75.81; H, 7.11;
N, 5.20. Found: C, 75.88; H, 7.18; N, 5.11.
N-(4-Chlorobenzyl)-N-(4-chlorophenyl)propionamide (3l)
White powder; m.p. 115–116ꢀC. IR (KBr): 3026, 2873, 1662, 1512,
827, 804. 1H NMR (500 MHz, CDCl3): d 7.11 (m, 6H, H-Ar), 6.87
(d, J = 8.0 Hz, 2H, H-Ar), 4.85 (s, 2H, NCH2), 2.10 (q, J = 7.4 Hz, 2H,
CH2), 1.1 (t, J = 7.4 Hz, 3H, Me). 13C NMR (125 MHz, CDCl3): d 10.1
(Me), 28.2 (CH2-CO), 52.7 (CH2N), 127.9, 129.1, 130.4, 130.6, 136.3
(Cipso), 141.0 (C-Cl), 141.6 (C-Cl), 142.2 (C-N)), 174.0 (CO). MS (E.I.)
N-(4-Methoxybenzyl)-N-p-tolylpropionamide (3f)
Yellow light powder; m.p. 128–129ꢀC. IR (KBr): 3032, 2924, 1662,
1508, 1028, 817, 740.1H NMR (500 MHz, CDCl3): d 7.14 (d,
J = 8.3Hz, 4H, H-Ar), 7.85 (d, J = 8.2Hz, 2H, H-Ar), 6.8 (d, J = 8.2Hz,
2H, H-Ar), 4.82 (s, 2H, NCH2), 3.81 (s, 3H, OMe), 2.37 (s, 3H, Me),
2.08 (q, J = 7.4Hz, 2H, CH2), 1.1 (t, J = 7.4Hz, 3H, Me). 13C NMR
(125 MHz, CDCl3): d 10.1 (Me-CH2), 21.1 (Me-Ar), 28.4 (CH2-CO),
52.9 (CH2N), 55.9 (OMe), 114.0 (CH), 128.3 (CH), 129.0 (CH), 130.4
(CH), 133.5 (C-Me), 137.2 (Cipso), 139.9 (C-N) 159.0 (C-OMe), 174.4
(CO). MS (E.I.) (70 eV): m/z (%) 283 (M+, 25), 226 (5), 176 (5), 121
(100), 91 (8), 77 (8). Anal. Calcd for C18H21NO2: C, 76.29; H, 7.47; N,
4.94. Found: C, 76.17; H, 7.38; N, 5.07.
Table 1. Synthesis of amide 3
N-(4-Methoxybenzyl)-N-phenylpropionamide (3h)
Product 3
R
R′
R”
Yield (%)a
White powder; m.p. 98–99ꢀC. IR (KBr): 3061, 2935, 1662, 1510,
1
1031, 842, 777. H NMR (500 MHz, CDCl3): d 7.34 (m, 3H, H-Ar),
a
b
c
C6H5
C6H5
C6H5
C6H5
C6H5
C6H5
Me
Et
85
81
82
80
76
73
80
76
78
77
84
80
76
72
70
76
81
7.12 (d, J = 2.7 Hz, 2H, H-Ar), 6.98 (d, J = 8.5 Hz, 2H, H-Ar), 6.81
(d, J = 8.5Hz, 2H, H-Ar), 4.85 (s, 2H, NCH2), 3.80 (s, 3H, OMe), 2.08
(q, J = 7.3 Hz, 2H, CH2), 1.09 (t, J = 7.3Hz, 3H, Me). 13C NMR
(125 MHz, CDCl3): d 10.1 (Me-CH2), 28.2 (CH2-CO), 52.7 (CH2N), 55.6
(OMe), 114.1 (CH), 128.2 (CH), 128.9 (CH), 129.8 (CH), 130.3 (CH),
136.6 (Cipso), 142.8 (C-N) 159.2 (C-OMe), 174.1 (CO). MS (E.I.)
(70 eV): m/z (%) 269 (M+, 18), 212 (5), 121 (100), 104 (5), 91 (6), 77 (8).
Anal. Calcd for C17H19NO2: C, 75.81; H, 7.11; N, 5.20. Found: C, 75.75;
H, 7.04; N, 5.15.
4-Cl-C6H4
4-Cl-C6H4
4-Me-C6H4
4-Me-C6H4
C6H5
Me
Et
d
e
f
4-MeO-C6H4
4-MeO-C6H4
4-MeO-C6H4
4-MeO-C6H4
4-Me-C6H4
4-Me-C6H4
4-Cl-C6H4
4-Cl-C6H4
4-Cl-C6H4
4-Me-C6H4
4-Me-C6H4
C6H5
Me
Et
g
h
i
Me
Et
C6H5
4-Cl-C6H4
4-Cl-C6H4
4-Cl-C6H4
4-Cl-C6H4
4-Me-C6H4
4-Me-C6H4
4-Me-C6H4
C6H11
Me
Et
j
k
l
Me
Et
N-(4-Chlorobenzyl)-N-p-tolylacetamide (3i)
Cream powder; m.p. 173–175ꢀC. IR (KBr): 3001, 2858, 1658, 1512,
825, 802. 1H NMR (500 MHz, CDCl3): d 7.25 (d, J= 2.6 Hz, 2H, H-Ar), 7.16
(m, 4H, H-Ar), 6.87 (d, J= 5.8 Hz, 2H, H-Ar), 4.85 (s, 2H, NCH2), 2.38
(s, 3H, Me), 1.9 (s, 3H, Me). 13C NMR (125 MHz, CDCl3): d 21.2 (Me-Ar),
28.4 (Me-CO), 52.6 (CH2N), 127.3 (CH), 128.8 (CH), 129.4 (CH), 130.2
(CH), 133.1 (C-Me), 136.9 (Cipso), 141.8 (C-Cl), 142.1 (C-N)), 172.4 (CO).
MS (E.I.) (70 eV): m/z (%) 273 (M+, 85), 231 (100), 180 (3), 162 (3), 125
m
n
o
p
q
Me
Me
Et
Me
Me
C6H5
CH2CH(Me)2
aIsolated yield.
wileyonlinelibrary.com/journal/aoc
Copyright © 2012 John Wiley & Sons, Ltd.
Appl. Organometal. Chem. 2012, 26, 103–107