ACCEPTED MANUSCRIPT
condition and washing (hexane, 15 mL) the resulting solid gave 1b (0.59 g, 96%) as white
~
solid. FTIR (KBr):
= 3461, 3056, 2950, 1838, 1615, 1584, 1559, 1057, 1451, 1365, 1275,
1
1237, 1142, 957, 824, 753, 693, 667, 630, 559, 549, 544, 453 cm-1. H NMR (400 MHz,
CD3OD) δ = 7.80 (d, J = 8.7 Hz, 1H), 7.52 (t, J = 8.0 Hz, 2H), 7.29 (d, J = 7.7 Hz, 1H), 7.16
(t, J = 7.7 Hz, 1H), 7.04 (t, J = 7.4 Hz, 1H), 6.94 – 6.89 (m, 2H), 6.72 (d, J = 8.0 Hz, 1H),
6.56 (t, J = 7.5 Hz, 1H), 5.80 (s, 1H), 3.21 – 2.86 (m, 2H), 2.61 – 2.31 (m, 2H), 1.82 – 1.68
(m, 4H).13C NMR (101 MHz, DMSO-d6) δ = 156.4, 154.6, 132.4, 129.4, 129.3, 129.2, 129.0,
128.3, 127.8, 126.9, 122.8, 121.7, 120.3, 120.2, 117.7, 116.0, 61.3, 51.6 (br. 2C) 23.5 (2C).
HRMS (ESI) exact mass calculated for C21H22NO2 ([M + H]+): 320.1645; found: 320.1641.
<Suppl. Fig. 2 & 3>
1-((2-hydroxyphenyl)(4-methylpiperazin-1-yl)methyl)naphthalen-2-ol (1c): According to
GP: 2-napthol (0.20 g, 1.39 mmol), salicylaldehyde (0.17 mL, 1.66 mmol), N-methyl
piperazine (0.18 mL, 1.66 mmol) in benzene 2 mL in reflux condition for 16 h, slow
evaporation under ambient condition and washing (50 mL; EtOAc : hexane; 1 : 15) the
~
resulting solid gave 1c (0.42 g, 90%) as white powder. FTIR (KBr):
= 3458, 3061, 3045,
2956, 2806, 1622, 1601, 1577, 1517, 1459, 1332, 1283, 1239, 1152, 1139, 1096, 997, 949,
832, 813, 760, 754, 746, 636, 533 cm-1. 1H NMR (400 MHz, CDCl3) δ = 13.87 (s, 1H), 7.83
(d, J = 8.6 Hz, 1H), 7.68 (d, J = 8.5 Hz, 2H), 7.37 – 7.31 (m, 1H), 7.30 – 7.26 (m, 1H), 7.19
(d, J = 7.6 Hz, 1H), 7.17 – 7.15 (m, 1H), 7.04 – 7.00 (m, 1H), 6.68 (t, J = 8 Hz, 1H), 6.60 (d,
J = 8.0 Hz, 1H), 6.05 (s, 1H), 3.32 – 3.29 (m, 1H), 3.12 – 3.09 (m, 1H), 3.04 – 2.91 (m, 3H),
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2.69 – 2.66 (m, 1H), 2.60 – 2.56 (m, 1H), 2.53 (s, 3H), 2.38 – 2.32 (m, 1H). C NMR (101
MHz, CDCl3) δ = 156.2, 155.2, 133.2, 130.6, 129.5, 129.3, 128.8, 128.7, 126.8, 125.3, 122.7,
121.9, 120.3, 119.9, 116.1, 114.9, 62.5, 55.9, 55.3, 52.7, 47.1, 45.8. HRMS (ESI) exact mass
calculated for C22H25N2O2 ([M + H]+): 349.1911; found: 349.1904.
<Suppl. Fig. 4 & 5>
1-((4-methylpiperazin-1-yl)(phenyl)methyl)naphthalen-2-ol (1f): According to GP: 2-
napthol (1.0 g, 6.94 mmol), benzaldehyde (0.84 mL, 8.32 mmol), N-methylpiperazine (0.923
mL, 8.32 mmol) in benzene 2 mL in reflux condition for 18 h, slow evaporation under
ambient condition, washing the solid residue (60 mL; EtOAc : hexane; 1 : 10), gave 1f as
~
yellowish solid (1.82 g, 80%). FTIR (KBr):
= 3439, 3061, 2970, 2839, 2798, 1620, 1598,
1581, 1520, 1473, 1452, 1415, 1265, 1238, 1154, 1136, 1083, 1016, 999, 949, 834, 817, 748,
698, 637, 514, 497 cm-1. 1H NMR (400 MHz, CD3OD): δ = 13.34 (s, 1H), 7.82 (d, J = 8.6 Hz,
1H), 7.64 (t, J = 8.6 Hz, 1H), 7.55 – 7.53 (m, 2H), 7.35 – 7.31 (m, 1H), 7.24 – 7.20 (m, 3H),
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