J IRAN CHEM SOC
(s, 1H, CH), 6.77 (td, J = 7.4, 1.2 Hz, 1H, Ar), 6.96 (td,
J = 7.8, 1.2 Hz, 2H, Ar), 7.16–7.21 (m, 1H, Ar), 7.29–7.42
(m, 8H, Ar), 7.53 (d, J = 7.2 Hz, 2H, Ar), 12.39 (br s, 1H,
OH) ppm; 13C NMR (100 MHz, CDCl3): δ = 39.1, 59.6,
75.5, 116.9, 119.2, 125.4, 127.5, 128.1, 128.6, 128.7,
128.8, 129.0, 129.1, 129.3, 137.2, 138.8, 156.9 ppm.
(ddd, J = 8.0, 7.6, 1.6 Hz, 1H, Ar), 7.35 (d, J = 8.0 Hz, 2H,
Ar), 11.80 (s, 1H, OH) ppm; 13C NMR (100 MHz, CDCl3):
δ = 52.1, 55.2, 66.9, 76.0, 114.2, 116.9, 119.5, 125.1,
128.5, 129.3, 129.7, 131.3, 156.0, 159.3 ppm.
2‑((6‑Methoxynaphthalen‑2‑yl)(morpholino)methyl)phenol
(4j)
2‑((Benzylamino)(phenyl)methyl)phenol (4f)
Yield: 96 %; mp: 115–120 °C; 1H NMR (400 MHz,
CDCl3): δ = 2.48–2.52 (m, 2H, 2NCH), 2.66 (br s, 2H,
2NCH), 3.77–3.79 (m, 4H, 2OCH2), 3.91 (s, 3H, OCH3),
4.56 (s, 1H, CH), 6.75 (td, J = 7.4, 1.0 Hz, 1H, Ar), 6.92
(dd, J = 8.2, 1.0 Hz, 1H, Ar), 7.01 (dd, J = 7.6, 1.6 Hz, 1H,
Ar), 7.11 (d, J = 2.4 Hz, 1H, Ar), 7.13–7.18 (m, 2H, Ar),
7.60 (d, J = 8.0 Hz, 1H, Ar), 7.70 (d, J = 8.8 Hz, 1H, Ar),
7.74 (d, J = 9.2 Hz, 1H, Ar), 7.77 (br s, 1H, Ar), 11.92 (br
s, 1H, OH) ppm; 13C NMR (100 MHz, CDCl3): δ = 52.3,
55.3, 66.9, 76.9, 105.6, 117.0, 119.1, 119.6, 124.8, 126.4,
127.5, 127.8, 128.6, 128.7, 129.4, 129.5, 134.2, 134.5,
156.1158.0 ppm; MS: m/z 349.1 (M+). Anal. Calcd for
C22H23NO3 (349.42): C, 75.62; H, 6.63; N, 4.01. Found: C,
75.55; H, 6.69; N, 4.07.
1
Yield: 82 %; mp: 67–71 °C [34]; H NMR (400 MHz,
CDCl3): δ = 1.40 (br s, 1H, NH), 4.64 (d, J = 15.6 Hz,
1H, NCHPh), 4.92 (d, J = 15.6 Hz, 1H, NCHPh), 5.32
(s, 1H, CH), 6.97 (td, J = 7.6, 1.8 Hz, 1H, Ar), 7.09 (d,
J = 6.8 Hz, 2H, Ar), 7.22–7.26 (m, 1H, Ar), 7.35–7.44 (m,
8H, Ar), 7.53 (d, J = 7.2 Hz, 2H, Ar), 12.52 (br s, 1H, OH)
ppm; 13C NMR (100 MHz, CDCl3): δ = 55.3, 63.2, 117.7,
119.6, 126.7, 128.6, 128.7, 128.8, 128.9, 129.2, 129.3,
130.0, 131.2, 137.6, 138.1, 159.7 ppm.
2‑(Morpholino(m‑tolyl)methyl)phenol (4g)
Yield: 90 %; mp: 119–121 °C; 1H NMR (400 MHz,
CDCl3): δ = 2.36 (s, 3H), 2.47–2.51 (m, 2H, 2NCH),
2.64 (br s, 2H, 2NCH), 3.78–3.79 (m, 4H, 2OCH2), 4.41
(s, 1H, CH), 6.76 (td, J = 7.4, 1.0 Hz, 1H, Ar), 6.90 (dd,
J = 8.0, 1.2 Hz, 1H, Ar), 6.99 (dd, J = 7.6, 1.6 Hz, 1H, Ar),
7.10 (d, J = 7.2 Hz, 1H, Ar), 7.13–7.18 (m, 1H, Ar), 7.22
(t, J = 7.6 Hz, 1H, Ar), 7.27 (br s, 2H, Ar), 11.80 (s, 1H,
OH) ppm; 13C NMR (100 MHz, CDCl3): δ = 21.6, 52.3,
66.9, 76.9, 117.0, 119.6, 124.9, 125.5, 128.6, 128.8, 128.9,
129.1, 129.4, 138.6, 139.3, 156.1 ppm.
2‑((4‑Chlorophenyl)(morpholino)methyl)phenol (4k)
1
Yield: 70 %: mp: 109–112 °C [35]; H NMR (400 MHz,
CDCl3): δ = 2.42–2.45 (m, 2H, 2NCH), 2.58 (br s, 2H,
2NCH), 3.74–3.80 (m, 4H, 2OCH2), 4.38 (s, 1H, CH), 6.74
(td, J = 7.4, 1.2 Hz, 1H, Ar), 6.87–6.94 (m, 2H, Ar), 7.14
(ddd, J = 8.0, 7.6, 1.6 Hz, 1H, Ar), 7.28 (d, J = 8.4 Hz,
2H, Ar), 7.38 (d, J = 8.4 Hz, 2H, Ar), 11.55 (br s, 1H, OH)
ppm; 13C NMR (100 MHz, CDCl3): δ = 52.1, 66.7, 76.0,
117.1, 119.7, 124.3, 128.8, 129.0, 129.1, 129.7, 133.8,
137.8, 155.8 ppm.
2‑((4‑(Tert‑butyl)phenyl)(morpholino)methyl)phenol (4h)
Yield: 94 %; mp: 130–135 °C; 1H NMR (400 MHz, CDCl3):
δ = 1.29 (s, 9H, 3CH3), 2.53 (br s, 2H, 2NCH), 2.64 (br
s, 2H, 2NCH), 3.80 (br s, 4H, 2OCH2), 4.45 (s, 1H, CH),
6.75 (t, J = 3.0 Hz, 1H, Ar), 6.89 (d, J = 8.0 Hz, 1H, Ar),
7.01 (d, J = 7.2 Hz, 1H, Ar), 7.15 (t, J = 7.2 Hz, 1H, Ar),
7.33 (d, J = 8.0 Hz, 2H, Ar), 7.37 (d, J = 8.0 Hz, 2H, Ar),
8.74 (br s, 1H, OH) ppm; 13C NMR (100 MHz, CDCl3):
δ = 31.2, 34.5, 52.2, 66.7, 76.3, 116.9, 119.6, 124.7, 125.8,
128.2, 128.6, 129.4, 135.7, 151.1, 156.0 ppm; MS: m/z
325.2 (M+). Anal. Calcd for C21H27NO2 (325.44): C, 77.50;
H, 8.36; N, 4.30. Found: C, 77.54; H, 8.31; N, 4.23.
2‑(Phenyl(phenylamino)methyl)phenol (4l)
1
Yield: 10 %; Oil; H NMR (400 MHz, CDCl3): δ = 4.31
(br s, 1H, NH), 5.59 (s, 1H, CH), 6.80–6.83 (m, 1H, Ar),
6.85 (td, J = 7.4, 1.2 Hz, 1H, Ar), 6.89–6.93 (m, 2H, Ar),
6.98 (dd, J = 8.0, 1.6 Hz, 1H, Ar),7.18–7.24 (m, 3H, Ar),
7.30–7.36 (m, 3H, Ar), 7.37–7.41 (m, 3H, Ar), 9.37 (br s,
1H, OH) ppm; 13C NMR (100 MHz, CDCl3): δ = 72.8,
114.2, 114.8, 117.1, 118.3, 119.6, 123.9, 127.3, 130.0,
130.3, 130.6, 131.0, 135.2, 154.1, 160.5 ppm.
2‑((4‑Methoxyphenyl)(morpholino)methyl)phenol (4i)
4‑(((2‑Hydroxyphenyl)(phenyl)methyl)amino)benzonitrile
(4m)
1
Yield: 97 %; mp: 103–107 °C [33]; H NMR (400 MHz,
1
CDCl3): δ = 2.45–2.47 (m, 2H, 2NCH), 2.61 (br s, 2H,
2NCH), 3.79 (s, 3H, OCH3), 3.80–3.81 (m, 4H, 2OCH2),
4.39 (s, 1H, CH), 6.74 (td, J = 7.4, 1.2 Hz, 1H, Ar), 6.84–
6.89 (m, 3H, Ar), 6.95 (dd, J = 7.6, 1.6 Hz, 1H, Ar), 7.14
Yield: 87 %; mp: 84–89 °C; H NMR (400 MHz, CDCl3):
δ = 4.68 (br s, 1H, NH) 5.63 (s, 1H, CH), 6.99 (td, J = 7.5,
0.9 Hz, 1H, Ar), 7.09–7.11 (m, 1H, Ar), 7.36–7.40 (m,
2H, Ar), 7.43–7.49 (m, 2H, Ar), 7.51–7.55 (m, 1H, Ar),
1 3