Paper
.53 (s, 2H), 2.66 (s, 2H), 4.38 (s, 1H), 6.73 (t, 1H, J ¼ 7.2 Hz, MHz, CDCl
RSC Advances
2
3
): d 23.83, 25.80, 52.28, 75.85, 110.20, 111.72, 127.85,
ArH), 6.87 (d, 1H, J ¼ 7.8 Hz, ArH), 6.96–6.99 (m, 1H, ArH), 7.09– 128.06, 128.55, 128.83, 129.00, 130.94, 133.84, 137.52, 155.92
7
8
2
1
.14 (m, 1H, ArH), 7.30 (t, 2H, J ¼ 8.4 Hz, ArHs), 7.41 (d, 2H, J ¼ ppm.
13
.4 Hz, ArHs), 12.31 (s, 1H, OH); C NMR (75 MHz, CDCl ): d
2,4-Dibromo-6-[morpholin-4-yl(phenyl)methyl]phenol, 6m.
3
ꢀ
3.46, 31.30, 34.43, 53.18, 75.29, 116.78, 119.04, 125.52, 126.91, White solid; mp 167–170 C; IR (KBr): 3365, 3007, 2850, 1603,
ꢂ1
1
27.39, 128.22, 128.27, 138.97, 150.43, 156.70 ppm.
-Bromo-2-(phenyl)(piperidin-1-yl)methylphenol, 6g. Pale 2.58 (s, 2H), 3.72–3.84 (m, 4H), 4.40 (s, 1H), 7.04 (d, 1H, J ¼ 2.4
yellow sticky mass, IR (KBr): 3440, 3015, 2945, 2860, 1610, 608 Hz, ArH), 7.32–7.37 (m, 2H, ArHs), 7.53 (s, 3H, ArHs), 7.54 (s,
3
1110, 610 cm ; H NMR (CDCl , 300 MHz): d 2.44–2.51 (m, 2H),
4
ꢂ1
1
13
cm ; H NMR (CDCl
3 3
, 300 MHz): d 1.27–1.35 (m, 2H), 1.49–1.65 1H, ArH), 13.02 (s, 1H, OH); C NMR (75 MHz, CDCl ): d 51.95,
(
7
m, 6H), 2.41 (s, 2H), 4.43 (s, 1H), 6.75 (d, 1H, J ¼ 8.7 Hz, ArH), 66.66, 76.25, 111.00, 111.73, 127.44, 128.46, 128.78, 129.24,
.0–7.01 (d, 1H, J ¼ 8.7, ArH), 7.18–7.22 (dd, 1H, J ¼ 8.5 & 2.4 Hz, 131.13, 134.18, 137.65, 152.60 ppm.
ArH), 7.31–7.37 (m, 3H, ArHs), 7.55–7.63 (m, 1H, ArH), 7.68–7.72
2-(3,5-Dichlorophenyl)(piperidin-1-yl)methylphenol, 6n. White
): d solid; mp 127–129 C; IR (KBr): 3450, 3012, 2850, 1608, 1110, 610
1
3
ꢀ
(m, 1H, ArH), 12.74 (s, 1H, OH); C NMR (75 MHz, CDCl
3
ꢂ1
1
2
1
1
4.00, 26.00, 52.46, 76.03, 110.62, 118.76, 120.50, 127.60, cm ; H NMR (CDCl
28.15, 128.60, 128.84, 129.14, 131.10, 131.67, 135.39, 138.68, (s, 4H), 4.37 (s, 1H), 6.71–6.76 (m, 1H, ArH), 6.88 (d, 2H, J ¼ 7.8
56.43 ppm. Hz, ArHs), 7.13–7.26 (m, 1H, ArH), 7.27 (s, 1H, ArH), 7.33 (s, 2H,
-Bromo-2-(4-t-butylphenyl)(morpholino)methylphenol, 6h. ArHs), 12.50 (s, 1H, OH); C NMR (75 MHz, CDCl
3
, 300 MHz): d 1.51 (s, 2H), 1.68 (s, 4H), 2.42
1
3
4
3
): d 23.99,
ꢀ
White solid; mp 168–170 C; IR (KBr): 3350, 3008, 2857, 1605, 25.98, 52.75, 75.88, 117.30, 119.36, 124.27, 126.93, 128.10, 128.90,
ꢂ1
1
1
2
6
7
1
5
1
113 cm ; H NMR (CDCl , 300 MHz): d 1.31 (s, 9H, 3 ꢃ CH ), 128.95, 135.25, 143.24, 156.73 ppm.
3
3
.42–2.49 (m, 2H), 2.58 (s, 2H), 3.75–3.78 (m, 4H), 4.34 (s, 1H),
.76 (d, 1H, J ¼ 8.7 Hz, ArH), 7.08 (d, 1H, J ¼ 2.4 Hz, ArH), 7.20– oil; IR (KBr): 3450, 3010, 2855, 1600, 1238, 1118 cm ; H NMR
.24 (dd, 1H, J ¼ 8.7 & 2.4 Hz, ArH), 7.28–7.36 (m, 4H, ArHs), (CDCl , 300 MHz): d 1.47 (s, 2H), 1.64–1.67 (m, 4H), 2.42 (s, 4H),
): d 31.22, 34.53, 3.76 (s, 3H), 4.48 (s, 1H), 6.28 (dd, 1H, J ¼ 8.4 and 2.7 Hz, ArH),
2.18, 66.83, 75.98, 111.13, 118.86, 125.92, 128.16, 131.37, 6.44–6.45 (d, 1H, J ¼ 2.4 Hz, ArH), 6.77 (d, 1H, J ¼ 8.4 Hz, ArH),
31.91, 135.31, 151.44, 155.48 ppm. 7.27–7.30 (m, 1H, ArH), 7.32–7.35 (m, 4H, ArHs), 7.37–7.40 (m,
-(4-t-Butylphenyl)(piperidin-1-yl)methylphenol, 6i. White 2H, ArHs), 12.50 (s, 1H, OH); C NMR (75 MHz, CDCl ): d 24.14,
5-Methoxy-2-[phenyl(piperidin-1-yl)methyl]phenol, 6o. Sticky
ꢂ1
1
3
1
3
1.88 (s, 1H, OH); C NMR (75 MHz, CDCl
3
1
3
2
3
ꢀ
solid; mp 93–95 C; IR (KBr): 3415, 3045, 2945, 2855, 1610, 26.10, 52.32, 55.13, 75.80, 102.10, 105.18, 117.87, 127.70, 128.57,
ꢂ1
1
cm ; H NMR (CDCl , 300 MHz): d 1.30 (s, 9H, 3 ꢃ CH ), 1.64 128.86, 129.75, 139.44, 158.45, 160.09 ppm.
3
3
(
m, 2H), 1.66 (s, 4H), 2.44 (s, 4H), 4.46 (s, 1H), 6.68–6.73 (t, 1H, J
2-(4-Methoxyphenyl)(piperidine-1-yl)methylphenol; 6p. Sticky
ꢂ1
1
¼
7.5 Hz, ArH), 6.85–6.93 (m, 2H, ArHs), 7.09–7.28 (m, 1H, ArH), solid; IR (KBr): 3450, 3008, 2857, 1605, 1240, 1115 cm ; H NMR
1
3
7
.32 (s, 4H, ArHs), 12.62 (s, 1H, OH); C NMR (75 MHz, CDCl
d 24.14, 26.10, 31.31, 34.47, 52.52, 76.09, 116.77, 118.98, 125.51, 4H), 3.79 (s, 3H), 4.49 (s, 1H), 6.72 (t, 1H, J ¼ 7.2 Hz, ArH), 6.85–
25.84, 128.19, 128.41, 129.19, 136.28, 150.60, 157.17 ppm. 6.92 (m, 4H, ArHs), 7.10–7.16 (m, 1H, ArH), 7.32–7.35 (m, 2H,
-(4-Chlorophenyl)(morpholino)methylphenol, 6j. White ArHs), 12.73 (s, 1H, OH); C NMR (75 MHz, CDCl ): d 19.39,
3 3
): (CDCl , 300 MHz): d 1.48 (s, 2H), 1.65 (s, 2H), 1.66 (s, 2H), 2.43 (s,
1
1
3
2
3
ꢀ
solid; mp 108–110 C; IR (KBr): 3355, 3010, 2857, 1605, 1110, 21.37, 47.58, 50.47, 70.86, 109.20, 112.07, 114.24, 121.07, 123.49,
6
ꢂ1
1
05 cm ; H NMR (CDCl , 300 MHz): d 2.43–2.49 (m, 2H), 2.60 124.41, 126.63, 152.44, 154.39 ppm.
3
(
s, 2H), 3.74–3.78 (m, 4H), 4.40 (s, 1H), 6.75 (t, 1H, J ¼ 7.2 Hz),
4-Bromo-2-[(4-methoxyphenyl)(dibenzylamino)methyl]phenol,
ꢀ
ꢂ1
6
8
.89–6.96 (m, 2H, ArHs), 7.13–7.18 (m, 1H, ArH), 7.29 (d, 2H, J ¼ 6q. Solid; mp 147–149 C; IR (KBr): 3417, 2852, 1606, 1250 cm
;
2
),
1
.4 Hz, ArHs), 7.40 (d, 2H, J ¼ 8.4 Hz, ArHs), 11.58 (s, 1H, OH);
H NMR (CDCl
): d 52.24, 66.80, 76.10, 117.24, 119.81, 3.90 (s, 3H), 3.95 (d, 2H, J ¼ 13.2 Hz, ArCH
24.38, 128.97, 129.16, 129.26, 129.87, 134.01, 137.86, 155.95 (d, 1H, J ¼ 8.7 Hz, ArH), 6.95 (d, 1H, J ¼ 2.1 Hz, ArH), 7.03 (d, 2H,
J ¼ 8.7 Hz, ArHs), 7.29 (m, 1H, ArH), 7.29 (m, 1H, ArH), 7.30 (m,
-Bromo-2-(4-t-butylphenyl)(pyrrolidin-1-yl)methylphenol, 6k. 2H, ArHs), 7.31–7.33 (m, 6H, ArHs), 7.36 (s, 2H, ArHs), 7.39–7.41
3
, 300 MHz): d 3.39 (d, 2H, J ¼ 7.8 Hz, ArCH
1
3
C NMR (75 MHz, CDCl
3
2
), 5.11 (s, 1H), 6.86
1
ppm.
4
ꢀ
ꢂ1
1
13
Mp 132–133 C; IR (KBr): 3445, 3062, 2828, 1603, 1100 cm ; H (m, 2H, ArHs), 12.45 (s, 1H, OH); C NMR (75 MHz, CDCl3):
NMR (CDCl ), 1.85–1.87 (m, d 53.87, 55.36, 67.08, 110.81, 114.10, 126.31, 126.97, 127.76,
H), 2.52–2.65 (m, 4H), 4.32 (s, 1H), 6.76 (d, 1H, J ¼ 8.7 Hz, ArH), 128.74, 129.77, 131.64, 131.88, 132.15, 136.78, 156.89,
.1 (d, 1H, J ¼ 2.4 Hz, ArH), 7.18 (dd, 1H, J ¼ 6 and 2.4 Hz, ArH) 159.68 ppm.
.29 (t, 1H, J ¼ 2.4 Hz, ArH), 7.31 (d, 1H, J ¼ 2.1 Hz, ArH), 7.35– 4,6-Dichloro-2-[(phenyl)(dibenzylamino)methyl]phenol, 6r.
3
, 300 MHz): d 1.29 (s, 9H, 3 ꢃ CH
3
4
7
7
7
1
3
ꢀ
.38 (d, 2H, J ¼ 6.3 Hz, ArHs), 12.35 (s, 1H, OH); C NMR (75 Yellow solid; mp 122–125 C; IR (KBr): 3322, 3018, 2862, 1602,
ꢂ1
1
MHz, CDCl ): d 23.42, 31.28, 34.49, 53.19, 74.70, 110.70, 118.70, 660 cm ; H NMR (CDCl , 300 MHz): d 3.40 (d, 2H, J ¼ 13.2 Hz,
3
3
1
25.69, 127.37, 128.70, 130.89, 131.04, 138.09, 150.89, 155.92 ArCH ), 3.93–3.97 (d, 2H, J ¼ 13.2 Hz, ArCH ), 5.12 (s, 1H), 6.80
2
2
ppm.
(d, 1H, J ¼ 2.4 Hz, ArH), 6.90 (d, 1H, J ¼ 8.4 Hz, ArH), 7.15 (dd,
2
,4-Dibromo-2-(phenyl)(piperidin-1-yl)methylphenol, 6l. White 1H, J ¼ 8.7 and 2.4 Hz, ArH), 7.29 (s, 2H, ArH), 7.30–7.33 (m, 3H,
ꢀ
ꢂ1
solid; mp 118–120 C; IR (KBr): 3750, 3066, 2940, 2849, 1605 cm
;
ArHs), 7.36 (s, 2H, ArHs), 7.38–7.45 (m, 4H, ArHs), 7.47–7.49 (m,
1
13
3 3
H NMR (CDCl , 300 MHz): d 1.46 (m, 2H), 1.65–1.68 (m, 4H), 2.44 3H, ArHs), 12.24 (s, 1H, OH); C NMR (75 MHz, CDCl ): d 49.10,
(
m, 4H), 4.49 (s, 1H), 6.98 (d, 1H, J ¼ 2.4 Hz, ArH), 7.34 (s, 5H, 63.14, 113.28, 118.87, 121.37, 123.01, 123.89, 123.98, 125.00,
13
ArHs), 7.53 (d, 1H, J ¼ 2.1 Hz, ArH), 8.2 (s, 1H, ArH); C NMR (75 125.00, 129.95, 131.91, 151.52 ppm.
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RSC Adv., 2015, 5, 70586–70594 | 70593