6074 J . Org. Chem., Vol. 64, No. 16, 1999
Katritzky et al.
Hz, 1H), 7.71-7.65 (m, 4H), 7.37 (t, J ) 6.9, 1H), 7.26-7.14
(m, 2H), 5.14 (s, 1H), 3.86 (s, 3H), 3.34-1.33 (m, 10H); 13C
NMR δ 166.5, 155.5, 144.9, 132.2, 130.0, 129.7, 128.9, 128.6,
126.5, 122.4, 120.7, 120.0, 115.4, 71.6, 52.0., 26.0, 24.0. Anal.
Calcd for C24H25 NO3: C, 76.80; H, 6.71; N, 3.73. Found: C,
77.20; H, 7.01, N, 3.59.
1-[(4-Meth oxyp h en yl)(1-p yr r olid in yl)m eth yl]-2-n a p h -
th ol (6e). Hexanes/ethyl acetate (9:1) was used as the eluent
to give 6e in 74% yield as a pale yellow solid, mp 113-115 °C:
1H NMR δ 7.87 (d, J ) 8.2 Hz, 1H), 7.70 (t, J ) 10.2 Hz, 2H),
7.54 (d, J ) 8.0 Hz, 2H), 7.39 (t, J ) 6.7 Hz, 1H), 7.26-7.16
(m, 2H), 6.81 (d, J ) 7.6 Hz, 2H), 5.1 (s, 1H), 3.74 (s, 3H),
3.28-1.60 (m, 8H); 13C NMR δ 159.1, 155.4, 133.5, 131.8, 129.6,
129.3, 128.8, 128.6, 126.3, 122.3, 121.1, 119.9, 116.8, 113.9,
70.0, 55.2, 23.4. Anal. Calcd for C22H23 NO2: C, 79.24; H, 6.97;
N, 4.20. Found: C, 79.19; H, 6.89; N, 4.22.
4-Meth oxy-2-[m or p h olin o(p h en yl)m eth yl]p h en ol (6f).
Hexanes/ethyl acetate (10:1) was used as the eluent to give 6f
in 82% yield as colorless prisms, mp 87-89 °C: 1H NMR δ
11.22 (s, 1H), 7.44-7.42 (m, 2H), 7.32-7.26 (m, 3H), 6.81-
6.78 (m, 1H), 6.71-6.67 (m, 1H), 6.51 (s, 1H), 4.33 (s, 1H),
3.76-3.69 (m, 4H), 3.67 (s, 3H), 2.60-2.42 (m, 4H);13C NMR
δ 152.6, 149.7, 139.2, 128.9, 128.6, 128.1, 125.3, 117.4, 114.9,
113.7, 76.9, 66.8, 55.5, 52.2. Anal. Calcd for C18H21NO3: N, 4.68.
Found: N, 4.27. HRMS calcd for C18H21NO3: 299.1521, found
299.1522.
Meth yl 4-[(2-Hyd r oxy-5-m eth oxyp h en yl)(p ip er id in o)-
m eth yl]ben zoa te (6g). Hexanes/ethyl acetate (9:1) was used
as the eluent to give 6g in 80% yield as colorless prisms, mp
145-147 °C: 1H NMR δ 11.79 (s, 1H), 7.97 (d, J ) 7.5 Hz,
2H), 7.52 (br s, 2H), 6.89 (d, J ) 8.7 Hz, 1H), 6.70 (d, J ) 8.6
Hz, 1H), 6.46 (s, 1H), 4.43 (s, 1H), 3.90 (s, 3H), 3.66 (s, 3H),
2.52-2.39 (m, 4H), 1.65-1.49 (m, 6H); 13C NMR δ 166.7, 152.4,
150.5, 144.8, 130.1, 129.7, 128.6, 125.4, 117.4, 114.8, 113.5,
76.4, 55.6, 52.8, 52.1, 26.0, 24.0. Anal. Calcd for C21H25NO4
N, 3.94. Found: N, 3.95. HRMS calcd for C21H25 NO4: 355.1784,
found 355.1772.
4-Meth yl-2-[ph en yl(piper idin o)m eth yl]ph en ol (6l). Hex-
anes/ethyl acetate (9:1) was used as the eluent to give 6l in
80% yield as colorless prisms, mp 117-119 °C, lit.10 mp 112
°C: 1H NMR δ 12.25 (s, 1H), 7.41 (br s, 2H) 7.33-7.26 (m,
3H), 6.91 (d, J ) 8.2 Hz, 1H), 6.77 (d, J ) 7.9 Hz, 2H), 4.38 (s,
1H), 2.45-2.29 (m, 4H) 2.15 (s, 3H), 1.64-1.46 (m, 6H); 13C
NMR δ 154.5, 140.0, 129.6, 128.8, 128.7, 128.0, 127.8, 125.4,
116.6, 111.2, 76.7, 52.7, 26.1, 24.2, 20.5. Anal. Calcd for C19H23
-
NO: C, 81.10; H, 8.24; N, 4.98. Found: C, 81.01; H, 8.30; N,
4.98.
4-Isopr opyl-2-[m or ph olin o(ph en yl)m eth yl]ph en ol (6m ).
Hexanes/ethyl acetate (9:1) was used as the eluent to give 6m
in 76% yield as colorless prisms, mp 91-93 °C: 1H NMR δ
11.44 (s, 1H), 7.45-7.43 (m, 2H), 7.34-7.27 (m, 3H), 7.00 (d,
J ) 6.8 Hz, 1H), 6.79 (d, J ) 8.2 Hz, 2H), 4.37 (s, 1H), 3.76-
3.74 (m, 4H), 2.75-2.71 (m, 1H), 2.69-2.42 (m, 4 H), 1.14 (d,
J ) 6.8 Hz, 6H); 13C NMR δ 153.8, 139.8, 139.5, 128.8, 128.0,
127.3, 126.3, 124.3, 116.7, 77.0, 66.9, 52.3, 33.1, 24.2, 24.0.
Anal. Calcd for C20H25NO2: C, 77.13; H, 8.11; N, 4.50. Found:
C, 77.30; H, 8.51; N, 4.64.
4-Met h yl-2-[m or p h olin o(p h en yl)m et h yl]p h en ol (6n ).
Hexanes/ethyl acetate (9:1) was used as the eluent to give 6n
in 78% yield as a colorless solid, mp 87-88 °C: 1H NMR δ
11.45 (s, 1H), 7.45-7.43 (m, 2H), 7.33-7.26 (m, 3H), 6.93 (d,
J ) 8.2 Hz, 1H), 6.79-6.76 (m, 2H), 4.33 (s, 1H), 3.80-3.75
(m, 4H), 2.60-2.17 (m, 4H), 2.17 (s, 3H); 13C NMR δ 153.5,
139.6, 129.8, 129.2, 128.9, 128.6, 128.5, 128.0, 124.5, 116.8,
77.0, 66.9, 52.4, 20.4. Anal. Calcd for C18H21NO2: C, 76.29; H,
7.48; N, 4.94. Found: C, 76.46; H, 7.19; N, 4.92.
3-[P h en yl(p ip er id in o)m eth yl][1,1-bip h en yl]-4-ol (6o).
Hexanes/ethyl acetate (9:1) was used as the eluent to give 6o
in 76% yield as colorless prisms, mp 132-134 °C: 1H NMR δ
12.70 (s, 1H), 7.45-7.20 (m, 11H), 7.13 (s, 1H), 6.92 (d, J )
8.3 Hz, 1H), 4.52 (s, 1H), 2.44-2.30 (m, 4H), 1.67-1.27 (m,
6H);13C NMR δ 156.8, 141.0, 139.5, 132.1, 128.7, 128.6, 127.9,
127.0, 126.5, 126.3, 125.8, 117.3, 76.7, 52.6, 26.1, 24.1. Anal.
Calcd for C24H25NO: C, 83.92; H, 7.35; N, 4.08. Found: C,
83.70; H, 7.51; N, 4.05
4-Ch lor o-2-[m or p h olin o(p h en yl)m et h yl]p h en ol (6h ).
Hexanes/ethyl acetate (8:2) was used as the eluent to give 6h
in 73% yield as a colorless solid, mp 101-103 °C: 1H NMR δ
11.85 (s, 1H), 7.42-7.28 (m, 5H), 7.10 (d, J ) 8.4 Hz, 1H),
6.94 (s, 1H), 6.82 (d, J ) 8.5 Hz, 1H), 4.37 (s, 1H), 3.78-3.77
(m, 4H), 2.60-2.44 (m, 4H);13C NMR δ 154.7, 138.3, 129.3,
129.0, 128.9, 128.5, 126.2, 124.0, 118.4, 116.6, 76.2, 66.7, 52.0.
Anal. Calcd for C17H18ClNO2: C, 67.21; H, 5.98; N, 4.61.
Found: C, 67.27; H, 6.26; N, 4.63.
4-Br om o-2-[(4-m eth ylp h en yl)(1,4-th ia zin a n -4-yl)m eth -
yl]p h en ol (6i). Hexanes/ethyl acetate (9:1) was used as the
eluent to give 6i in 75% yield as colorless prisms, mp 158-
160 °C: 1H NMR δ 11.97 (s, 1H), 7.29-7.17 (m, 5H), 7.02 (s,
1H), 6.77 (d, J ) 8.5 Hz, 1H), 4.52 (s, 1H), 2.90-2.55 (m, 8 H),
2.37 (s, 3H); 13C NMR δ 155.8, 138.3, 134.4, 131.9, 131.5, 129.7,
128.7, 126.9, 118.8, 111.0, 75.5, 53.0, 28.0, 21.1. Anal. Calcd
for C18H20BrNOS: C, 57.15; H, 5.33; N, 3.70. Found: C, 57.41;
H, 5.69; N, 3.67.
2-[Mor p h olin o(p h en yl)m et h yl]p h en ol (6j). Hexanes/
ethyl acetate (9:1) was used as the eluent to give 6j in 66%
yield as colorless prisms, mp 117-119 °C: 1H NMR δ 11.72
(s, 1H), 7.43-7.41 (m, 2H), 7.32-7.22 (m, 3H), 7.12 (t, J ) 8.0
Hz, 1H), 6.94 (d, J ) 7.5 Hz, 1H), 6.86 (d, J ) 8.0 Hz, 1H),
6.72 (t, J ) 7.4 Hz, 1H), 4.40 (s, 1H), 3.80-3.73 (m, 4H), 2.59-
2.42 (m, 4H); 13C NMR δ 156.1, 139.3, 129.4, 128.9, 128.7,
128.5, 128.1, 124.8, 119.6, 117.0, 76.8, 66.9, 52.2. Anal. Calcd
for C17H19NO2: C, 75.80; H, 7.12; N, 5.20. Found: C, 75.72; H,
7.14; N, 5.19.
3,5-Dim eth yl-2-[m or ph olin o(ph en yl)m eth yl]ph en ol (6k).
Hexanes/ethyl acetate (8:2) was used as the eluent to give 6k
in 77% yield as a colorless solid, mp 159-161 °C: 1H NMR δ
12.36 (s, 1H), 7.46 (d, J ) 5.5 Hz, 2H), 7.30-7.23 (m, 3H),
6.59 (s, 1H), 6.41 (s, 1H), 4.49 (s, 1H), 3.75 (br s, 4H), 3.10-
2.34 (m, 4H), 2.21 (s, 3H), 2.14 (s, 3H);13C NMR δ 156.4, 138.5,
138.4, 136.6, 129.2, 128.8, 128.0, 122.7, 120.3, 115.8, 72.6, 66.8,
52.6, 21.0, 19.7. Anal. Calcd for C19H23NO2: C, 76.73, H, 7.80,
N, 4.71. Found: C, 76.55, H, 7.86, N, 4.67.
4-P h en yl-2-[(4-m eth ylp h en yl)(1,4-th ia zin a n -4-yl)m eth -
yl]p h en ol (6p ). Hexanes/ethyl acetate (9:1) was used as the
eluent to give 6p in 72% yield as colorless prisms, mp 169-
171 °C: 1H NMR δ 11.89 (s, 1H), 7.43-7.23 (m, 7H), 7.20-
7.13 (m, 4H), 6.94-6.92 (d, J ) 8.3 Hz, 1H), 4.60 (s, 1H), 2.85-
2.75 (m, 8H), 2.31 (s, 3H); 13C NMR δ 156.2, 140.8, 138.0, 135.2,
132.5, 129.6, 128.78, 128.6, 128.1, 127.2, 126.5, 126.4, 125.1,
117.4, 76.2, 53.2, 28.1, 21.1. Anal. Calcd for C24H25NOS: N,
3.73. Found: N, 3.52. HRMS calcd for C24H25NOS: 375.1657,
found 375.1651.
1-[Mor p h olin o(4-n itr op h en yl)m eth yl]-2-n a p h th ol (6q).
Hexanes/ethyl acetate (9:1) was used as the eluent to give 6q
in 51% yield as a yellow solid, mp 177-179 °C: 1H NMR δ
12.81 (s,1H), 8.12(d, J ) 8.2 Hz, 2H), 7.79(d, J ) 5.6, 3H),
7.71 (d, J ) 2.3 Hz, 2H), 7.42 (t, J ) 7.2 Hz, 1H), 7.26 (t, J )
7.4 Hz, 1H), 7.16 (d, J ) 8.9 Hz, 1H), 5.24 (s, 1H), 3.82-3.70
(m, 4H), 3.12-2.44 (m, 4H); 13C NMR δ 154.7, 147.6, 146.1,
131.9, 130.5, 129.8, 129.1, 128.9, 127.0, 124.2, 123.0, 120.3,
119.8, 113.8, 71.0, 66.7. Anal. Calcd for C21H20N2O4: N, 7.69.
Found: N, 7.72.
4-Me t h oxy-2-[m or p h olin o(4-p yr id in yl)m e t h yl]p h e -
n ol (7a ). Chloroform/methanol (50:1) was used as the eluent
to give 7a in 78% yield as a yellow solid, mp 148-150 °C: 1H
NMR δ 10.72 (s, 1H), 8.50 (d, J ) 5.2 Hz, 2H), 7.34 (d, J ) 5.2
Hz, 2H), 6.76 (d, J ) 8.8 Hz, 1H), 6.69-6.65 (m, 1H), 6.47 (d,
J ) 2.5 Hz, 1H), 4.24 (s, 1H), 3.71 (br s, 4H), 3.64 (s, 3H),
2.68-2.48 (m, 2H), 2.48-2.36 (m, 2H); 13C NMR δ 152.8, 150.4,
149.4, 148.0, 123.8, 123.1, 117.7, 114.6, 114.2, 75.9, 66.6, 55.6,
52.3. Anal. Calcd for C17H20N2O3: C, 67.98; H, 6.71; N, 9.33.
Found: C, 67.88; H, 6.88; N, 9.30.
4-Br om o-2-[m or ph olin o(4-pyr idin yl)m eth yl]ph en ol (7b).
Chloroform/methanol (100:1) was used as the eluent to give
7b in 74% yield as a yellow solid, mp 175-177 °C: 1H NMR δ
11.40 (s, 1H), 8.56 (d, J ) 4.5 Hz, 2H), 7.37 (d, J ) 4.8 Hz,
2H), 7.24 (d, J ) 8.6 Hz, 1H), 7.11 (s, 1H), 6.77 (d, J ) 8.7 Hz,
1H), 4.35 (s, 1H), 3.75 (br s, 4H), 2.70-2.50 (m, 2H), 2.50-
2.40 (m, 2H); 13C NMR δ 155.0, 150.4, 147.4, 131.9, 131.4,