1
Mp: 89-90°C. Yield: 24%; H NMR (600 MHz, CD
3
OD) δ: 1.67–1.47 (m, 4H),
2
2
6
.14–1.98 (m, 4H), 2.67–2.52 (m, 4H), 3.57–3.46 (m, 4H), 4.20 (s, 2H), 5.27 (s,
H), 6.06 (dd, J= 7.9, 1.8 Hz, 1H), 6.08 (s, 1H), 6.14 (dd, J= 8.0, 1.8 Hz, 1H),
.80 (d, J= 7.6 Hz, 2H), 6.86 (t, J= 8.0 Hz, 1H), 7.05 (d, J= 7.9 Hz, 2H), 7.19 (d,
J= 8.0 Hz, 2H), 7.22 (d, J= 7.9 Hz, 2H), 7.25 (d, J= 8.0 Hz, 2H), 8.14 (d, J= 7.6
1
3
Hz, 2H). C NMR (151 MHz, CD
7.95, 49.68 x 2, 61.66, 100.92, 105.11, 106.40, 109.63 x 2, 128.33 x 2, 129.33
x 2, 129.44 x 2, 130.45 x 2, 130.66, 133.47, 138.84, 142.12, 142.88 x 2, 145.21,
3
OD) δ: 26.10 x 2, 31.87, 32.00, 36.22, 36.25,
4
+
+
1
51.64, 155.12, 159.16. HRMS m/z [M-Br] calcd. for C33
38 3
H N O : 492.3009,
found: 492.1705.
4
.1.5.5. 4-(dimethylamino)-1-{4-[(3-hydroxyphenylamino)-
methyl]benzyl}pyridinium bromide (4e).
1
Yield: 27%; H NMR (300 MHz, CD
3
OD) δ: 3.21 (s, 6H), 4.27 (s, 2H), 5.32 (s,
2
9
2
5
1
H), 6.02 (d, J= 7.2 Hz, 1H), 6.05 (s, 2H), 6.10 (d, J= 7.2 Hz, 1H), 6.83 (t, J=
.0, 1H), 6.95 (d, J= 7.9 Hz, 2H), 7.32 (d, J= 8.4 Hz, 2H), 7.40 (d, J= 8.4 Hz,
H), 8.19 (d, J= 7.9 Hz, 2H). C NMR (126 MHz, DMSO-d ) δ: 39.75 x 2, 45.99,
9.11, 99.21, 103.36, 103.85, 107.97 x 2, 127.62 x 2, 127.92 x 2, 129.34,
1
3
6
+
33.95, 141.32, 141.93 x 2, 149.78, 155.85, 158.04. HRMS m/z [M-H] calcd.
+
for C21
H
22
N
3
OBr : 412.1024, found: 412.1059.
4
.1.5.6. 4-(dimethylamino)-1-({4-[(3-hydroxyphenylamino)-
methyl]biphenyl-4-yl}methyl)pyridinium bromide (4f).
1
Mp: 249-251°C. Yield: 40%; H NMR (300 MHz, DMSO-d
(
6
) δ: 3.18 (s, 6H), 4.24
d, J= 6.0 Hz, 2H), 5.44 (s, 2H), 5.95 (dd, J= 8.0, 2.2 Hz, 1H), 5.99 (t, J= 2.1 Hz,
1
1
7
H), 6.04 (dd, J= 7.9, 1.8 Hz, 1H), 6.16 (t, J= 6.0 Hz, 1H), 6.79 (t, J= 7.9 Hz,
H), 7.06 (d, J= 7.8 Hz, 2H), 7.42 (d, J= 8.3 Hz, 2H), 7.47 (d, J= 8.2 Hz, 2H),
.60 (d, J= 8.3 Hz, 2H), 7.69 (d, J= 8.2 Hz, 2H), 8.45 (d, J= 7.8 Hz, 2H), 8.87
1
3
(
1
1
bs, 1H). C NMR (75 MHz, DMSO-d
6
) δ: 40.50 x 2, 46.79, 59.77, 99.99,
04.08, 104.66, 108.76 x 2, 127.32 x 2, 127.85 x 2, 128.39 x 2, 129.30 x 2,
30.10, 135.39, 138.35, 141.01, 141.15, 142.76 x 2, 150.64, 156.64, 158.83.
+
HRMS m/z [M-Br] calcd. for C27
28 3
H N O: 410.2232, found: 410.2241.
4
.1.5.7. 4-(dimethylamino)-1-(4-{4-[(3-hydroxyphenylamino)-
methyl]phenethyl}benzyl)pyridinium bromide (4g).
1
Yield: 39%; H NMR (300 MHz, CD
3
OD) δ: 2.83 (m, 4H), 3.17 (s, 6H), 4.17 (s,
2
6
8
2
3
1
1
4
H), 5.25 (s, 2H), 6.04 (d, J= 2.3 Hz, 1H), 6.07 (s, 1H,), 6.11 (d, J= 2.2 Hz, 1H),
.13 (t, J= 3 Hz, 1H), 6.83 (t, J= 8.3 Hz, 1H), 6.89 (d, J= 7.9 Hz, 2H), 7.01 (d, J=
.2 Hz, 2H), 7.14 (d, J= 8.1 Hz, 2H), 7.19 (d, J= 8.1 Hz, 2H), 7.24 (d, J= 8.2 Hz,
H), 7.98 (s, 1H), 8.11 (d, J= 7.9 Hz, 2H). C NMR (75 MHz, CD OD) δ: 37.13,
7.34, 39.29 x 2, 47.29, 60.44, 99.84, 103.96, 105.30, 107.93 x 2, 127.19 x 2,
28.34 x 2, 128.49 x 2, 129.50 x 2, 129.59, 132.37, 138.01, 139.91, 141.76 x 2,
1
3
3
+
+
43.15, 150.46, 156.70, 158.03. HRMS m/z [M-Br] calcd. for C29
38.2545, found: 438.2561.
H
32
N
3
O :
4
.1.5.8. 4-(dimethylamino)-1-[4-(4-{4-[(3-hydroxyphenylamino)-
methyl]phenyl}butyl)benzyl]pyridinium bromide (4h).