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HETEROCYCLES, Vol. 87, No. 8, 2013
4-Acetyl-N-(4-(dimethylamino)benzyl)-N-methylbenzamide (3d); Yield 88%; as a yellow oil; IR (KBr)
νmax 2924, 1658, 1633, 1522, 1447, 1315, 1067, 925, 703 cm-1; 1H NMR (400 MHz, CDCl3) δ 7.99~7.96
(m, 2H), 7.56 (d, J = 8.2 Hz, 1H), 7.52 (d, J = 8.0 Hz, 1H), 7.25 (d, J = 8.4 Hz, 1H), 7.00 (d, J = 8.4 Hz,
1H), 6.73 (d, J = 8.4 Hz, 1H), 6.70 (d, J = 8.4 Hz, 1H), 4.66 (s, 1H), 4.36 (s, 1H), 3.02 (s, 1.5H), 2.93 (s,
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6H), 2.80 (s, 1.5H), 2.62 (d, J = 12.3 Hz, 3H); C NMR (100 MHz, CDCl3) δ 197.42, 170.99, 170.28,
150.15, 140.91, 137.56, 129.56, 128.50, 127.79, 127.08, 124.29, 123.30, 112.65, 54.51, 50.19, 40.52,
36.45, 32.85, 26.70; HRMS (EI+) Calcd for C19H22N2O2 [M]+ 310.1681, found 310.1682.
4-Benzoyl-N-(4-(dimethylamino)benzyl)-N-methylbenzamide (3e); Yield 73%; as a yellow oil; IR
(KBr) νmax 3730, 3626, 2923, 2354, 1636, 1523, 1351, 1067, 863, 807, 724 cm-1; 1H NMR (400 MHz,
CDCl3) δ 7.86~7.79 (m, 4H), 7.60~7.47 (m, 5H), 7.27~7.26 (m, 1H), 7.03 (d, J = 8.6 Hz, 1H), 6.74 (d, J
= 8.2 Hz, 1H), 6.71(d, J = 8.4 Hz, 1H), 4.68 (s, 1H), 4.41 (s, 1H), 3.04 (s, 1.5H), 2.96 (s, J = 9.0 Hz, 6H),
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2.84 (s, 1.5H); C NMR (100 MHz, CDCl3) δ 196.08, 171.08, 170.36, 162.24, 150.15, 140.24, 138.33,
137.14, 132.85, 130.15, 129.56, 128.39, 127.81, 126.67, 124.32, 123.35, 122.60, 112.63, 54.58, 50.21,
40.52, 36.64, 32.89; HRMS (EI+) Calcd for C24H24N2O2 [M]+ 372.1838, found 372.1837.
N-(4-(Dimethylamino)benzyl)-3,4-dimethoxy-N-methylbenzamide (3f); Yield 88%; as a yellow oil; IR
(KBr) νmax 3332, 2940, 2834, 1635, 1510, 1351, 1270, 1233, 1132, 1032, 768, 630 cm-1; 1H NMR (400
MHz, CD3OD) δ 7.22 (br, 1H), 7.05~6.95 (m, 4H), 6.77 (d, J = 8.4 Hz, 2H), 6.98 (d, J = 8.0 Hz, 1H),
6.71 (dd, J = 11.6, 8.4 Hz, 2H), 4.66~4.33 (m, 2H), 3.85 (s, 3H), 3.72 (s, 1.5H), 2.97 (s, 1.5H), 2.91 (s,
6H); 13C NMR (100 MHz, CDCl3) δ 150.1, 148.8, 129.4, 128.8, 127.7, 124.5, 120.0, 112.7, 110.8, 110.5,
60.4, 55.9, 40.6, 38.6; HRMS (EI+) Calcd for C19H24N2O3 [M]+ 328.1787, found 328.1790.
N-(4-(Dimethylamino)benzyl)-N-methyl-2-phenylacetamide (3g); Yield 85%; as a yellow oil; IR
(KBr) νmax 3466, 2924, 1645, 1522, 1455, 1398, 1348, 1164, 1105, 946, 809, 727, 697, 571 cm-1; 1H NMR
(400 MHz, CDCl3) δ 7.24~7.34 (m, 5H), 7.12 (d, J = 8.4 Hz, 1H), 6.95 (d, J = 8.4 Hz, 1H), 6.68 (t, J =
8.0 Hz, 2H), 4.46 (dd, J = 33.6 Hz, 2H), 3.77 (dd, J = 12.8 Hz, 3H), 2.94 (dd, J = 6.4 Hz, 6H), 2.89 (dd, J
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= 19.6 Hz, 3H); C NMR (400 MHz, CDCl3) δ 171.1, 150.1, 135.3, 129.4, 128.8, 128.6, 127.6, 126.7,
125.1, 123.9, 112.7, 53.2, 50.3, 41.3, 41.0, 40.6, 34.9, 33.7; HRMS (EI+) Calcd for C18H22N2O [M]+
282.1732, found 282.1725.
N-(4-(Dimethylamino)benzyl)-N-methyldecanamide (3h); Yield 75%; as a colorless oil; IR (KBr) νmax
1
3466, 2924, 1652, 1521, 1456, 1399, 1348, 1226, 1163, 947, 802 cm-1; H NMR (400 MHz, CDCl3) δ
7.13 (d, J = 8.4 Hz, 1H), 7.03 (d, J = 8.8 Hz, 1H), 6.67~6.72 (m, 2H), 4.46 (dd, J = 23.6 Hz, 2H), 2.94 (d,
J = 6 Hz, 6H), 2.89 (dd, J = 9.6 Hz, 3H), 2.31~2.41 (m, 2H), 1.26 (br, 14H), 0.88 (t, J = 4.4 Hz, 3H); 13C
NMR (400 MHz, CDCl3) δ 173.5, 173.1, 150.1, 129.3, 127.4, 125.5, 124.2, 112.7, 52.9, 50.1, 40.6, 34.5,
33.7, 33.5, 33.2, 31.9, 29.4, 25.6, 25.2, 22.7, 14.1; HRMS (EI+) Calcd for C20H34N2O [M]+ 318.2671,
found 318.2670.