HETEROCYCLES, Vol. 82, No. 1, 2010
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for 3.5 h the solution was concentrated under reduced pressure. Purification of the residue by flash
chromatography (pentane/EtOAc, 4:1) provided 17c (1.30 g, 90%) as a colorless solid. Rf = 0.22
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(pentane/EtOAc, 4:1). H-NMR (300 MHz, CDCl3): δ = 0.85 (t, J = 6.6 Hz, 3 H, 12´-H3), 1.051.35 (m,
18 H, 3´-H2 to 11´-H2), 1.68 (m, 2 H, 2´-H2), 2.86 (t, J = 7.8 Hz, 2 H, 1´-H2), 5.23 (s, 2 H, -CH2Ph), 6.63
(s, 1 H, 3-H), 7.18 (dd, J = 9.0, 2.4 Hz, 1 H, 7-H), 7.287.48 (m, 5 H, 5 × Ph-H), 7.62 (d, J = 2.4 Hz, 1 H,
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5-H), 7.71 (d, J = 9.0 Hz, 1 H, 8-H), 12.08 (sbr, 1 H, OH) ppm. C-NMR (75 MHz, CDCl3): δ = 14.12
(C-12´), 22.67 (C-11´), 29.32, 29.36, 29.41, 29.46, 29.60, 30.32, 31.90, 38.50 (C-1´ to C-10´), 69.95
(-CH2Ph), 100.9, 104.6 (C-3, C-5), 121.6 (C-4a), 122.1 (C-7), 127.1 (2 Ph-Co), 127.8, 128.1 (C-8,
Ph-Cp), 128.6 (2 Ph-Cm), 135.8, 142.2 (C-8a, Ph-Ci), 155.4, 160.7, 161.0 (C-2, C-4, C-6) ppm. IR
(KBr): ̃ = 2921, 2850, 1620, 1591, 1531, 1466, 1390, 1351, 1323, 1268, 1220, 1184, 1163, 1096, 998,
834, 738, 696, 630, 604, 560, 472 cm-1. UV (MeOH): λmax (lg ) = 234.0 (4.730), 277.5 (3.806), 287.0
(3.709), 322.5 (3.604), 332.5 nm (4.618). MS (ESI): m/z (%) = 420.2 (100) [M+H]+. HRMS (ESI): calcd.
for C28H37NO2 + H+ 420.2897; found 420.2897.
4-Benzyloxy-6-[2-(dimethylamino)ethoxy]-2-dodecylquinoline (18c): Sodium hydride (0.109 g,
2.74 mmol, 60% in mineral oil) was added slowly to a solution of 17c (0.499 g, 1.19 mmol) in DMF
(6 mL) at 0 °C. After stirring for 1 h at room temperature the solution was cooled to 0 °C,
2-dimethylaminoethyl chloride hydrochloride (0.180 g, 1.25 mmol) was added and the suspension was
stirred at 100 °C for 2 h. After cooling to room temperature the reaction was quenched by addition of H2O
(10 mL) and the mixture extracted with EtOAc (3 × 20 mL). The combined organic extracts were washed
with H2O (2 × 50 mL) and brine (50 mL), dried over Na2SO4 and concentrated under reduced pressure.
Purification of the residue by flash chromatography (CH2Cl2/MeOH, 30:1, 1% NEt3) provided 18c
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(0.572 g, 98%) as a colorless solid. Rf = 0.30 (CH2Cl2/MeOH, 30:1, 1% NEt3). H-NMR
(300 MHz, CDCl3): δ = 0.88 (t, J = 6.6 Hz, 3 H, 12´´-H3), 1.181.42 (m, 18 H, 3´´-H2 to 11´´-H2), 1.77
(m, 2 H, 2´´-H2), 2.38 (s, 6 H, N(CH3)2), 2.79 (t, J = 6.0 Hz, 2 H, 1-H2), 2.86 (t, J = 7.8 Hz, 2 H, 1´´-H2),
4.18 (t, J = 6.0 Hz, 2 H, 2-H2), 5.27 (s, 2 H, -CH2Ph), 6.67 (s, 1 H, 3´-H), 7.307.53 (m, 7 H, 5´-H, 7´-H,
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5 × Ph-H), 7.89 (d, J = 9.0 Hz, 1 H, 8´-H) ppm. C-NMR (150 MHz, CDCl3): δ = 14.08 (C-12´´), 22.63
(C-11´´), 29.31, 29.51, 29.60, 29.62, 30.15, 31.86, 39.65 (C-1´´ to C-10´´), 45.84 (N(CH3)2), 58.17 (C-1),
66.12 (C-2), 70.05 (-CH2Ph), 100.8, 101.1 (C-3´, C-5´), 120.5 (C-4a´), 121.9 (C-7´), 127.4 (2 Ph-Co),
128.2, 129.7 (C-8´, Ph-Cp), 128.6 (2 Ph-Cm), 135.9, 144.6 (C-8a´, Ph-Ci), 155.9, 160.3, 161.5 (C-2´,
C-4´, C-6´) ppm. IR (KBr): ̃ = 2920, 2850, 2769, 1598, 1568, 1503, 1468, 1359, 1266, 1222, 1077, 1032,
991, 838, 732, 697 cm-1. UV (CH3CN): λmax (lg ) = 235.0 (4.737), 273.5 (3.801), 317.5 (3.484),
330.0 nm (3.528). MS (ESI): m/z (%) = 491.3 (28) [M+H]+, 401.3 (100) [MCH2Ph+H]+. HRMS (ESI):