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The Journal of Organic Chemistry
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2-(1-(benzyl(methyl)amino)-3-phenylprop-2-yn-1-yl)-6-methoxyphenol (4k). It was obtained in
292.8 mg, 82% yield, yellow solid with m.p: 90-92 oC. 1H NMR (400 MHz, CDCl3) δ: 7.61-7.58
(2H, m), 7.40-7.38 (5H, m), 7.36-7.32 (2H, m), 7.30-7.26 (1H, m), 7.21 (1H, d, J = 8 Hz), 6.88-
6.85 (1H, m), 6.81 (1H, t, J = 8 Hz), 5.21 (1H, s), 3.88 (3H, s), 3.81 (2H, d, J = 4 Hz), 2.29 (3H,
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s). C{1H} NMR (100 MHz, CDCl3) δ: 148.0, 146.6, 136.7, 132.0, 129.5, 128.8, 128.8, 128.5,
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127.9, 122.5, 121.8, 120.4, 118.7, 111.7, 90.1, 81.6, 59.1, 58.8, 56.0, 36.8. HRMS (ESI--TOF)
m/z: [M+H]+ Calcd for C24H23NO2 358.1807; Found 358.1821.
2-(1-morpholino-3-phenylprop-2-yn-1-yl)-4-nitrophenol (4l). It was obtained in 246.8 mg, 73%
yield, cream solid with m.p: 142-144 oC. 1H NMR (600 MHz, CDCl3) δ: 8.56 (1H, s), 8.20-8.19
(1H, m), 7.61 (2H, d, J = 6 Hz), 7.48-7.39 (3H, m), 6.94 (1H, d, J = 8.4 Hz), 5.15 (1H, s), 3.85
(4H, s), 2.87(4H, s). 13C{1H} NMR (150 MHz, CDCl3) δ: 163.4, 140.5, 132.0, 129.2, 128.5, 126.2,
125.4, 121.4, 120.8, 116.9, 91.8, 79.6, 66.6, 60.6. MS (EI) m/z for C19H18N2O4: 338. The
spectroscopic data of 4l is consistent with the previously reported in literature.27
2-methoxy-6-(3-phenyl-1-(4-phenylpiperazin-1-yl)prop-2-yn-1-yl)phenol (4m). It was obtained in
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318.5 mg, 80% yield, yellow solid with m.p: 145-146 oC. H NMR (400 MHz, CDCl3) δ: 11.18
(1H, s), 7.55-7.50 (2H, m), 7.36-7.31 (4H, m), 7.29-7.22 (3H, m), 6.94-6.89 (4H, m), 5.21 (1H, s),
3.90 (3H, s), 3.27 (4H, s), 2.96 (4H, s).13C{1H} NMR (100 MHz, CDCl3) δ: 151.0, 148.2, 146.6,
132.2, 132.0, 129.3, 128.8, 128.5, 122.3, 121.2, 120.6, 120.4, 118.9, 116.6, 111.9, 90.2, 81.8, 60.4,
56.1, 49.5. MS (EI) m/z for C26H26N2O2: 398. HRMS (MALDI-TOF) m/z: [M+H]+ Calcd for
C26H26N2O2 399.2067; Found 399.2065.
2-(1-morpholino-3-(p-tolyl)prop-2-yn-1-yl)phenol (4n) It was obtained in 261 mg, 85% yield,
yellow solid with m.p: 89-91 oC. 1H NMR (600 MHz, CDCl3) δ: 10.83 (1H, s), 7.59 (1H, d, J = 6
Hz), 7.46 (2H, d, J = 6 Hz), 7.28-7.25 (1H, m), 7.19 (2H, d, J = 6 Hz), 6.92-6.88 (2H, m), 5.11
(1H, s), 3.82 (4H, s), 2.81 (4H, s), 2.41 (3H, s). 13C{1H} NMR (150 MHz, CDCl3) δ: 157.0, 138.9,
131.7, 129.7, 129.2, 128.8, 120.6, 119.4, 119.1, 116.4, 90.5, 80.8, 66.9, 60.7, 21.5. MS (EI) m/z
for C20H21NO2: 307. The spectroscopic data of 4n is consistent with the previously reported in
literature.5d,23b,28
2-(1-(piperidin-1-yl)-3-(p-tolyl)prop-2-yn-1-yl)phenol (4o) It was obtained in 250 mg, 82% yield,
yellow viscous liquid. 1H NMR (400 MHz, CDCl3) δ: 7.60 (1H, d, J = 8 Hz), 7.48 (2H, d, J = 8
Hz), 7.28-7.20 (3H, m), 6.89 (2H, m), 5.12 (1H, s), 3.07-2.57 (4H, m), 2.42 (3H, s), 1.88-1.47 (6H,
m). 13C{1H} NMR (100 MHz, CDCl3) δ: 157.6, 138.7, 131.7, 129.3, 129.1, 128.5, 121.4, 119.5,
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