N. Ullah · 1-Aryl-4-(biarylmethylene)piperazine Ligands
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8-(4-((4ꢀ-Fluorobiphenyl-4-yl)methyl)piperazin-1-yl)-2-
methoxyquinoline (3b)
4 H, piperazine H), 3.48 (br. s, 4 H, piperazine H), 3.74 (s,
2 H, NCH2Ar), 4.05 (s, 3 H,OCH3), 6.87 (d, J = 9.0 Hz,
1 H, 3-H), 7.09 (d, J = 8.2 Hz, 1 H, 5-H), 7.16 (d, J =
8.5 Hz, 2 H, aromatic H), 7.28 (m, 2 H, aromatic H), 7.34
(d, J = 8.2 Hz, 1 H, 7-H), 7.57 (m, 2 H, aromatic H), 7.93
(m, 2 H, 4-H, 4ꢀ-H), 8.60 (d, J = 2.0 Hz, I H, 2ꢀ-H), 8.73 (d,
J = 2.0 Hz, I H, 6ꢀ-H). – 13C NMR (CDCl3, 125.7 MHz):
δ = 50.94 (Cpiper), 52.86 (Cpiper), 53.18 (OCH3), 59.89
(NCH2Ar), 112.54, 116.05, 116.22, 116.70, 121.64, 124.30,
126.26, 128.99, 129.05, 133.52, 133.85, 135.47, 135.77,
139.82, 140.12, 147.07, 147.19, 149.24, 160.92, 164.23 (all
Carom). – C26H25FN4O (428.50): calcd. C 72.88, H 5.88,
N 13.08; found C 72.81, H 5.94, N 13.02.
Following the same procedure as adopted for the synthe-
sis of 3a, the title compound was obtained as a light-yellow
solid from the reductive amination of compound 3 in combi-
◦
nation with 6b (68 %). M. p. 136 – 137 C. – IR (neat): ν =
3058, 3044, 2988, 2972, 1626, 1574, 1465, 1240 cm−1. –
1H NMR (CDCl3, 500 MHz): δ = 2.83 (br. s, 4 H, piperazine
H), 3.48 (br. s, 4 H, piperazine H), 3.68 (s, 2 H, NCH2Ar),
4.04 (s, 3 H, OCH3), 6.87 (d, J = 8.8 Hz, 1 H, 3-H), 7.07 –
7.14 (m, 3 H, aromatic H), 7.27 (t, J = 8.8 Hz, 1 H, aro-
matic H), 7.34 (dd, J = 1.2, 7.9 Hz, 1 H, 5-H), 7.46 – 7.48
(m, 2 H, aromatic H), 7.51 – 7.57 (m, 4 H, aromatic H), 7.93
(d, J = 8.8 Hz, 1 H, 4-H). – 13C NMR (CDCl3, 125.7 MHz):
δ = 51.46 (Cpiper), 53.11 (Cpiper), 53.56 (OCH3), 62.83
(NCH2Ar), 112.40, 115.49, 115.66, 116.50, 121.32, 124.19,
126.11, 126.85, 128.51, 128.57, 129.71, 137.05, 137.25,
139.06, 139.60, 139.98, 147.24, 161.40, 163.36 (all Carom). –
C27H26FN3O (427.51): calcd. C 75.85, H 6.13, N 9.83;
found C 75.79, H 6.17, N, 9.76.
8-(4-(3-Cyclopentenylbenzyl)piperazin-1-yl)-2-methoxy-
quinoline (3e)
Following the same procedure as adopted for the synthe-
sis of 3a, the title compound was obtained as a light-yellow
solid from compounds 3 and 6e (57 %). M. p. 115 – 116 ◦C. –
IR (neat): ν = 3047, 3032, 2982, 2976, 2970, 1631, 1545,
1450, 1260 cm−1 (C-O). – 1H NMR (CDCl3, 500 MHz): δ =
2.02 (m, 2 H, cyclopent H), 2.53 (m, 2 H, cyclopent H), 2.73
(m, 2 H, cyclopent H), 2.79 (br. s, 4 H, piperazine H), 3.45
(br. s, 4 H, piperazine H), 3.62 (s, 2 H, NCH2Ar), 4.05 (s,
3 H, OCH3), 6.21 (s, 1 H, cyclopent H), 6.86 (d, J = 9.8 Hz,
1 H, 3-H), 7.08 (d, J = 7.3 Hz, 1 H, 5-H), 7.24 – 7.29 (m,
3 H, aromatic H), 7.32 (m, 2 H, aromatic H), 7.46 (br. s, 1 H,
3ꢀ-H), 7.94 (d, J = 8.5 Hz, 1 H, 4-H). – 13C NMR (CDCl3,
125.7 MHz): δ = 23.33 (Ccyclopent), 33.23 (Ccyclopent), 33.30
(Ccyclopent), 51.48 (Cpiper), 53.09 (Cpiper), 53.55 (OCH3),
63.29 (NCH2Ar), 112.34 (C-3), 116.49 (Ccyclopent), 121.21,
124.15, 124.32, 126.09, 126.17, 126.31, 127.74, 128.15,
136.74, 138.20, 139.54, 139.97, 142.40, 147.31, 160.51 (all
Carom). – C26H29N3O (399.53): calcd. C 78.16, H 7.32,
N 10.52; found C 78.11, H 7.37, N 10.47.
2-Methoxy-8-(4-((5-phenylpyridin-3-yl)methyl)piperazin-1-
yl)quinoline (3c)
Following the same procedure as adopted for the synthe-
sis of 3a, the title compound was obtained as an off-white
solid from compounds 3 and 6c (63 %). M. p. 131 – 132 ◦C. –
IR (neat): ν = 3068, 3045, 2982, 2976, 1636, 1570, 1455,
1242 cm−1. – 1H NMR (CDCl3, 500 MHz): δ = 2.86 (br. s,
4 H, piperazine H), 3.48 (br. s, 4 H, piperazine H), 3.73 (s,
2 H, NCH2Ar), 4.06 (s, 3 H,OCH3), 6.87 (d, J = 8.8 Hz, 1 H,
3-H), 7.08 (dd, J = 1.2, 7.8 Hz, 1 H, 5-H), 7.28 (t, J = 7.9 Hz,
1 H, aromatic H), 7.34 (dd, J = 1.2, 7.8 Hz, 1 H, aromatic
H), 7.40 (m, 1 H, aromatic H), 7.48 (t, J = 7.9 Hz, 2 H, aro-
matic H), 7.61 (d, J = 7.3 Hz, 2 H, aromatic H), 7.93 (d, J =
8.8 Hz, 1 H, 4-H), 7.98 (br. s, 1H, 4ꢀ-H), 8.59 (d, J = 1.5 Hz,
1 H, 2ꢀ-H), 8.77 (d, J = 2.1 Hz, 1 H, 6ꢀ-H). – 13C NMR
(CDCl3, 125.7 MHz): δ = 51.42 (Cpiper), 52.69 (Cpiper),
53.54 (OCH3), 59.74 (NCH2Ar), 112.33, 116.05, 116.22,
116.49, 121.40, 124.10, 126.05, 127.13, 128.13, 129.02,
133.42, 135.55, 136.54, 137.54, 139.62, 139.94, 146.88,
147.04, 148.89, 160.73, 164.23 (all Carom). – C26H26N4O
(410.51): calcd. C 76.07, H 6.38, N 13.65; found C 76.00,
H 6.42, N 13.60.
8-(4-((5-Cyclopentenylpyridin-3-yl)methyl)piperazin-1-yl)-
2-methoxyquinoline (3f)
Following the same procedure as adopted for the syn-
thesis of 3a, the title compound was obtained as a light-
yellow semi-solid from compounds 3 and 6f (47 %). – IR
(neat): ν = 3062, 3042, 2980, 2976, 2964, 1636, 1546, 1451,
1261 cm−1. – 1H NMR (CDCl3, 500 MHz): δ = 2.05 (m,
2 H, cyclopent H), 2.56 (m, 2 H, cyclopent H), 2.73 (m, 2 H,
cyclopent H), 2.80 (br. s, 4 H, piperazine H), 3.46 (br. s, 4 H,
piperazine H), 3.64 (s, 2 H, NCH2Ar), 4.07 (s, 3 H, OCH3),
6.31 (m, 1 H, cyclopent H), 6.88 (d, J = 8.8 Hz, 1 H, 3-H),
8-(4-((5-(4-Fluorophenyl)pyridin-3-yl)methyl)piperazin-1-
yl)-2-methoxyquinoline (3d)
Following the same procedure as adopted for the synthe- 7.08 (dd, J = 1.2, 7.8 Hz, 1 H, 5-H), 7.27 (m, 1 H, aromatic
sis of 3a, the title compound was obtained as a light-brown H), 7.35 (dd, J = 1.2, 7.9 Hz, 1 H, 7-H), 7.76 (br. s, 1 H, 4ꢀ-
solid from compounds 3 and 6d (54 %). M. p. 160 – 161 ◦C. – H), 7.96 (d, J = 8.8 Hz, 1 H, 4-H), 8.44 (d, J = 1.8 Hz, 1 H,
IR (neat): ν = 3058, 3040, 2988, 2973, 1646, 1572, 1448, 2ꢀ-H), 8.59 (d, J = 2.1 Hz, 1 H, 6ꢀ-H). – 13C NMR (CDCl3,
1238 cm−1. – 1H NMR (CDCl3, 500 MHz): δ = 2.86 (br. s, 125.7 MHz): δ = 23.20 (Ccyclopent), 32.95 (Ccyclopent), 33.40
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