550
N.B. Pham et al. / European Journal of Medicinal Chemistry 74 (2014) 541e551
J ¼ 7.2 Hz, 2H), 2.87 (t, J ¼ 7.2 Hz, 2H), 2.69 (t, J ¼ 7.3 Hz, 2H), 2.29 (t,
J ¼ 7.3 Hz, 2H), 2.19 (s, 6H), 1.65 (ddd, J ¼ 7.3 Hz, 2H). 13C NMR
(150 MHz, CDCl3) 139.7, 133.0, 130.9, 127.9, 127.5, 124.7, 58.2, 49.6,
48.3, 45.7 (ꢂ2), 36.9, 28.2. HRESIMS(þ): m/z calculated
[C13H22N2O1Br]þ 285.0960, found 285.0958.
HRESIMS(þ): m/z calculated [C13H22Cl1N2]þ 241.1466, found
241.1465.
4.7.35. N1-(3-Chlorophenethyl)-N3,N3-dimethylpropane-1,3-
diamine (48)
Obtained as white oil, 75% yield; 1H NMR (600 MHz, CDCl3) dH
7.28 (t, J ¼ 7.7 Hz, 1H), 7.26 (s, 1H), 7.24 (d, J ¼ 7.7 Hz, 1H), 7.16 (d,
J ¼ 7.7 Hz, 1H), 2.95 (t, J ¼ 6.9 Hz, 2H), 2.88 (t, J ¼ 6.9 Hz, 2H), 2.77 (t,
J ¼ 7.0 Hz, 2H), 2.35 (t, J ¼ 7.0 Hz, 2H), 2.20 (s, 6H), 1.72 (p, J ¼ 7.0 Hz,
2H). 13C NMR (150 MHz, CDCl3) 141.9, 134.4, 129.9, 129.0, 127.2,
126.6, 58.4, 50.8, 48.8, 45.5 (ꢂ2), 35.6, 27.1. HRESIMS(þ): m/z
calculated [C13H22Cl1N2]þ 241.1466, found 241.1461.
4.7.29. N1-(3-Bromophenethyl)-N3,N3-dimethylpropane-1,3-
diamine (42)
Obtained as yellow oil, 70% yield; 1H NMR (600 MHz, CDCl3) dH
7.35 (s, 1H), 7.33 (d, J ¼ 7.8 Hz, 1H), 7.16e7.11 (m, 2H), 2.85 (t,
J ¼ 7.1 Hz, 2H), 2.76 (t, J ¼ 7.1 Hz, 2H), 2.65 (t, J ¼ 7.0 Hz, 2H), 2.27 (t,
J ¼ 7.2 Hz, 2H), 2.18 (s, 6H), 1.62 (p, J ¼ 7.1 Hz, 2H). 13C NMR
(150 MHz, CDCl3) 142.7, 131.9, 130.1, 129.4, 127.5, 122.6, 58.2, 51.0,
48.4, 45.6 (ꢂ2), 36.2, 28.1. HRESIMS(þ): m/z calculated
[C13H22N2O1Br]þ 285.0960, found 285.0961.
4.7.36. N1-(4-Chlorophenethyl)-N3,N3-dimethylpropane-1,3-
diamine (49)
Obtained as white oil, 75% yield; 1H NMR (600 MHz, CDCl3) dH
7.24 (d, J ¼ 8.3 Hz, 2H), 7.13 (d, J ¼ 8.3 Hz, 2H), 2.83 (t, J ¼ 7.1 Hz, 2H),
2.76 (t, J ¼ 7.1 Hz, 2H), 2.63 (t, J ¼ 7.2 Hz, 2H), 2.26 (t, J ¼ 7.2 Hz, 2H),
1.62 (p, J ¼ 7.2 Hz, 2H). 13C NMR (150 MHz, CDCl3) 138.8,132.0,130.2
(ꢂ2), 128.6 (ꢂ2), 58.2, 51.1, 48.4, 45.6 (ꢂ2), 35.9, 28.1. HRESIMS(þ):
m/z calculated [C13H22Cl1N2]þ 241.1466, found 241.1463.
4.7.30. N1-(4-Bromophenethyl)-N3,N3-dimethylpropane-1,3-
diamine (43)
Obtained as yellow oil, 60% yield; 1H NMR (600 MHz, CDCl3) dH
7.40 (d, J ¼ 8.1 Hz, 2H), 7.07 (d, J ¼ 8.0 Hz, 2H), 2.83 (t, J ¼ 7.2 Hz, 2H),
2.74 (t, J ¼ 7.1 Hz, 2H), 2.64 (t, J ¼ 7.1 Hz, 2H), 2.26 (t, J ¼ 7.2 Hz, 2H),
2.17 (s, 6H), 1.63 (p, J ¼ 7.2 Hz, 2H). 13C NMR (150 MHz, CDCl3) 139.3,
131.6 (ꢂ2), 130.6 (ꢂ2), 120.0, 77.4, 76.9, 76.7, 58.1, 51.1, 48.4, 45.6
(ꢂ2), 35.9, 28.1. HRESIMS(þ): m/z calculated [C13H22N2O1Br]þ
285.0960, found 285.0959.
4.7.37. N1-(3-Chloro-4-methoxyphenethyl)-N3,N3-
dimethylpropane-1,3-diamine (50)
Obtained as pale yellow oil, 68% yield; 1H NMR (600 MHz,
CDCl3) dH 7.22 (s, 1H), 7.07 (d, J ¼ 8.3 Hz, 1H), 6.86 (d, J ¼ 8.3 Hz, 1H),
3.88 (s, 3H), 2.85 (t, J ¼ 7.0 Hz, 2H), 2.75 (t, J ¼ 7.0 Hz, 2H), 2.69 (t,
J ¼ 7.1 Hz, 2H), 2.29 (t, J ¼ 7.1 Hz, 2H), 2.17 (s, 6H), 1.66 (p, J ¼ 7.1 Hz,
2H). 13C NMR (150 MHz, CDCl3) 153.6, 133.1, 130.5, 128.1, 122.5,
112.4, 58.4, 56.4, 51.1, 48.7, 45.6 (ꢂ2), 35.0, 27.7. HRESIMS(þ): m/z
calculated [C14H24N2O1Cl]þ 271.1571, found 271.1563.
4.7.31. N1-(2-Fluorophenethyl)-N3,N3-dimethylpropane-1,3-
diamine (44)
Obtained as pale yellow oil, 70% yield; 1H NMR (600 MHz, CDCl3)
dH 7.23e7.15 (m, 2H), 7.05 (t, J ¼ 7.5 Hz, 1H), 7.00 (t, J ¼ 7.5 Hz, 1H),
2.85 (dq, J ¼ 11.1, 5.6 Hz, 4H), 2.66 (t, J ¼ 7.1 Hz, 2H), 2.28 (t,
J ¼ 7.1 Hz, 2H), 2.18 (s, 6H), 1.64 (p, J ¼ 7.1 Hz, 2H). 13C NMR
(150 MHz, CDCl3) 162.2, 131.1, 128.0, 127.2, 124.1, 115.5, 58.1, 50.0,
48.3, 45.6 (ꢂ2), 29.9, 28.1. HRESIMS(þ): m/z calculated
[C13H22F1N2]þ 225.1761, found 225.1752.
4.7.38. N1-(3,4-Dichlorophenethyl)-N3,N3-dimethylpropane-1,3-
diamine (51)
Obtained as pale yellow oil, 70% yield; 1H NMR (600 MHz, CDCl3)
dH 7.34 (d, J ¼ 8.2 Hz, 1H), 7.30 (d, J ¼ 2.0 Hz, 1H), 7.03 (dd, J ¼ 8.2,
2.0 Hz, 1H), 2.83 (t, J ¼ 7.1 Hz, 2H), 2.74 (t, J ¼ 7.1 Hz, 2H), 2.64 (t,
J ¼ 7.1 Hz, 2H), 2.27 (t, J ¼ 7.2 Hz, 2H), 2.17 (s, 6H), 1.62 (p, J ¼ 7.1 Hz,
2H). 13C NMR (150 MHz, CDCl3) 140.7, 132.4, 130.8, 130.4, 130.2,
128.3, 58.2, 50.8, 48.4, 45.7 (ꢂ2), 35.7, 28.1. HRESIMS(þ): m/z
calculated [C13H21Cl2N2]þ 275.1076, found 275.1073.
4.7.32. N1-(3-Fluorophenethyl)-N3,N3-dimethylpropane-1,3-
diamine (45)
Obtained as pale yellow oil, 75% yield; 1H NMR (600 MHz, CDCl3)
dH 7.23 (m, 1H), 6.97 (d, J ¼ 7.5 Hz, 1H), 6.89 (m, 1H), 6.85 (m, 1H),
2.85 (t, J ¼ 7.1 Hz, 2H), 2.78 (t, J ¼ 7.1 Hz, 2H), 2.64 (t, J ¼ 7.1 Hz, 2H),
2.26 (t, J ¼ 7.1 Hz, 2H), 2.17 (s, 6H), 1.63 (m, 2H). 13C NMR (150 MHz,
CDCl3) 163.9, 142.9, 130.0, 124.5, 115.7, 113.2, 58.1, 51.0, 48.4, 45.6
(ꢂ2), 36.2, 28.0. HRESIMS(þ): m/z calculated [C13H22F1N2]þ
225.1761, found 225.1752.
4.7.39. N1-(2,4-Dichlorophenethyl)-N3,N3-dimethylpropane-1,3-
diamine (52)
Obtained as white oil, 80% yield; 1H NMR (600 MHz, CDCl3) dH
7.37 (d, J ¼ 2.1 Hz, 1H), 7.25 (d, J ¼ 8.2 Hz, 1H), 7.19 (dd, J ¼ 8.2,
2.1 Hz, 1H), 2.97 (t, J ¼ 7.5 Hz, 2H), 2.91 (d, J ¼ 7.5 Hz, 2H), 2.76 (t,
J ¼ 6.8 Hz, 2H), 2.33 (t, J ¼ 6.8 Hz, 2H), 2.17 (s, 6H), 1.70 (p, J ¼ 6.8 Hz,
2H). 13C NMR (150 MHz, CDCl3) 134.9 (ꢂ2), 133.0, 132.1, 129.5, 127.3,
58.5, 48.9, 48.8, 45.5 (ꢂ2), 33.2, 27.0. HRESIMS(þ): m/z calculated
[C13H21Cl2N2]þ 275.1076, found 275.1079.
4.7.33. N1-(4-Fluorophenethyl)-N3,N3-dimethylpropane-1,3-
diamine (46)
Obtained as yellow oil, 70% yield; 1H NMR (600 MHz, CDCl3) dH
7.15 (dd, J ¼ 8.4, 5.6 Hz, 2H), 6.96 (t, J ¼ 8.7 Hz, 2H), 2.83 (t,
J ¼ 7.4 Hz, 2H), 2.76 (t, J ¼ 7.1 Hz, 2H), 2.64 (t, J ¼ 7.1 Hz, 2H), 2.26 (t,
J ¼ 7.2 Hz, 2H), 2.17 (s, 6H), 1.62 (p, J ¼ 7.1 Hz, 2H). 13C NMR
(150 MHz, CDCl3) 160.8, 135.9, 130.2 (ꢂ2), 115.4 (ꢂ2), 58.1, 51.4,
48.4, 45.6 (ꢂ2), 35.7, 28.1. HRESIMS(þ): m/z calculated
[C13H22F1N2]þ 225.1761, found 225.1755.
4.7.40. N1-(2,6-Dichlorophenethyl)-N3,N3-dimethylpropane-1,3-
diamine (53)
Obtained as white oil, 75% yield; 1H NMR (600 MHz, CDCl3) dH
7.27 (d, J ¼ 7.6 Hz, 2H), 7.06 (t, J ¼ 7.6 Hz, 1H), 3.12 (m, 2H), 2.83 (m,
2H), 2.71 (t, J ¼ 7.3 Hz, 2H), 2.31 (t, J ¼ 7.3 Hz, 2H), 2.21 (s, 6H), 1.67
(p, J ¼ 7.3 Hz, 2H). 13C NMR (150 MHz, CDCl3) 136.3, 135.7, 128.3
(ꢂ2), 127.9 (ꢂ2), 58.2, 48.1, 47.9, 45.7 (ꢂ2), 32.2, 28.2. HRESIMS(þ):
m/z calculated [C13H21Cl2N2]þ 275.1076, found 275.1077.
4.7.34. N1-(2-Chlorophenethyl)-N3,N3-dimethylpropane-1,3-
diamine (47)
Obtained as white oil, 75% yield; 1H NMR (600 MHz, CDCl3) dH
7.34 (dd, J ¼ 7.6, 1.5 Hz, 1H), 7.24 (dd, J ¼ 7.6, 1.5 Hz, 1H), 7.18 (td,
J ¼ 7.6, 1.5 Hz,1H), 7.14 (td, J ¼ 7.6,1.5 Hz,1H), 2.93 (t, J ¼ 7.2 Hz, 2H),
2.87 (t, J ¼ 7.2 Hz, 2H), 2.68 (t, J ¼ 7.1 Hz, 2H), 2.29 (t, J ¼ 7.1 Hz, 2H),
2.19 (s, 6H), 1.65 (p, J ¼ 7.1 Hz, 2H). 13C NMR (151 MHz, CDCl3) 137.9,
134.3,130.9,129.7,127.7,126.9, 58.2, 49.5, 48.3, 45.7 (ꢂ2), 34.3, 28.2.
4.7.41. N1-(2-Chloro-6-fluorophenethyl)-N3,N3-dimethylpropane-
1,3-diamine (54)
Obtained as yellow oil, 70% yield; 1H NMR (600 MHz, CDCl3) dH
7.15 (d, J ¼ 8.1 Hz, 1H), 7.11 (td, J ¼ 8.1, 5.9 Hz, 1H), 6.95 (td, J ¼ 8.1,