Med Chem Res (2013) 22:382–391
389
1-(3-[3-{4-(2-Chlorobenzyl)piperazin-1-
yl}propoxy]phenyl)ethanone (10)
chloroform layer was washed with saline and dried over
anhydrous sodium sulphate. Removal of the solvent under
vacuum afforded the crude product which was purified by
column chromatography using silica gel (60–80 mesh),
employing petroleum ether along with varying amounts of
ethyl acetate and methanol as solvent.
Yield 58.3 %. mp 284–287 °C. FTIR (KBr, cm-1): 3065,
2941, 1683, 1592, 1440, 1272, 1156, 1049, 1011, 830, 755,
1
and 687. H-NMR (400 MHz; CDCl3, d, J): 7.52 (dt, 1H,
J = 7.8, 1.2 Hz); 7.47–7.45 (m, 2H); 7.36–7.32 (m, 2H);
7.22 (dt, 1H, J = 7.8, 1.4 Hz); 7.17 (dt, 1H, J = 7.8,
1.4 Hz); 7.10 (dd, 1H, J = 8.2, 2.6 Hz); 4.06 (t, 2H,
J = 7.2 Hz); 3.63 (s, 2H), 2.57 (s, 3H), 2.55–2.51 (broad-
ened m, 10H); 2.00 (quintet, 2H, J = 7.2 Hz). MS [EI,
m/z (relative intensity)]: 389 (42.0) [M?2], 387 (100) [Mꢀ?],
261 (3.6) [M–(ClC6H4CH3], 125 (0.3) [ClC6H4CH2]. Anal.
Calcd. for C22H27N2O2Cl: C, 68.29; H, 7.03; N, 7.24. Found:
C, 67.90; H, 6.88; N, 7.08.
3-[3-{4-(4-Chlorobenzyl) piperazin-1-
yl}propoxy]benzaldehyde (7)
Yield 63.9 %. mp 275–278 °C. FTIR (KBr, cm-1): 3022,
2941, 2812, 1698, 1593, 1452, 1386, 1262, 1150, 1089,
1010, 933, 841, 760 and 681. 1H-NMR (400 MHz; CDCl3),
d: 9.89 (s, 1H); 7.38–7.36 (m, 2H); 7.30 (t, 1H,
J = 7.5 Hz); 7.22–7.18 (m, 4H); 7.11–7.08 (m, 1H); 4.00
(t, 2H, J = 7.4 Hz); 3.42 (s, 2H), 2.54–2.46 (broadened m,
10H); 1.96 (quintet, 2H, J = 7.4 Hz). MS [EI, m/z (relative
intensity)]: 375 (49.0) [M?2], 373 (100) [Mꢀ?], 262 (18)
[M–PhCl], 247 (10) [M–(ClC6H4CH3], 126 (1.8)
[ClC6H4CH3], 100, 99. Anal. Calcd. for C21H25N2O2Cl: C,
67.64; H, 6.76; N, 6.65. Found: C, 66.08; H, 6.12; N, 6.45.
3-[3-{4-(4-Chlorobenzoyl) piperazin-1-
yl}propoxy]benzaldehyde (11)
Yield 62.5 %. mp 298–300 °C. FTIR (KBr, cm-1): 3012,
2921, 2832, 1695, 1593, 1452, 1380, 1256, 1138, 1070, 1009,
1
923, 851, 765 and 670. H-NMR (400 MHz; CDCl3, d, J):
9.80 (s, 1H); 7.86 (d, 2H, J = 7.6 Hz); 7.74 (t, 1H,
J = 7.5 Hz); 7.56 (d, 2H, J = 7.6 Hz); 7.32–7.25 (m, 2H);
7.16 (dt, 1H, J = 7.5, 1.5 Hz); 4.02 (t, 2H, J = 7.4 Hz);
3.40–3.38 (m, 4H); 2.50–2.46 (broadened m, 6H); 1.85
(quintet, 2H, J = 7.4 Hz). MS [EI, m/z (relative intensity)]:
389 (49.0) [M?2], 387 (100) [Mꢀ?], 247 (18) [M–Cl
C6H4CHO], 140 (9.8) [ClC6H4CHO]. Anal. Calcd. for
C21H23N2O3Cl: C, 65.20; H, 5.99; N, 7.24. Found: C, 64.18;
H, 5.65; N, 7.08.
3-[3-{4-(2-Chlorobenzyl)piperazin-1-
yl}propoxy]benzaldehyde (8)
Yield 66.7 %. mp 274–277 °C. FTIR (KBr, cm-1): 3064,
2942, 2812, 1698, 1594, 1448, 1386, 1263, 1150, 1048,
1010, 933, 831, 754 and 683. 1H-NMR (400 MHz; CDCl3),
d: 9.96 (s, 1H); 7.46 (dd, 1H, J = 7.8, 1.5 Hz); 7.44–7.43
(m, 2H); 7.38 (t, 1H, J = 7.6 Hz); 7.35 (dd, 1H, J = 7.8,
1.5 Hz); 7.23 (td, 1H, J = 7.4, 1.5 Hz); 7.20–7.16 (m, 2H);
4.07 (t, 2H, J = 7.2 Hz); 3.63 (s, 2H), 2.56–2.48 (broad-
ened m, 10H); 2.00 (quintet, 2H, J = 7.2 Hz). MS [EI, m/
z (relative intensity)]: 375 (45.0) [M?2], 373 (100) [M.?],
262 (5.8) [M–PhCl], 247 (10) [M–(ClC6H4CH3], 125 (3.0)
[ClC6H4CH2], 100, 99. Anal. Calcd. for C21H25N2O2Cl: C,
67.64; H, 6.76; N, 6.65. Found: C, 66.68; H, 6.23; N, 6.55.
3-[3-{4-(2-Chlorobenzoyl) piperazin-1-
yl}propoxy]benzaldehyde (12)
Yield 66.5 %. mp 296–298 °C. FTIR (KBr, cm-1): 3022,
2911, 2820, 1688, 1590, 1445, 1376, 1248, 1140, 1065, 1015,
1
920, 856, 760 and 673. H-NMR (400 MHz; CDCl3, d, J):
9.76 (s, 1H); 7.83 (t, 1H, J = 7.6 Hz); 7.66–7.62 (m, 2H);
7.48 (td, 1H, J = 7.6, 1.4 Hz); 7.42–7.37 (m, 3H); 7.22 (dt,
1H, J = 7.6, 1.5 Hz); 4.00 (t, 2H, J = 8.0 Hz); 3.41–3.39
(broadened m, 4H); 2.52–2.46 (broadened m, 6H); 1.82
(quintet, 2H, J = 8.0 Hz). MS [EI, m/z (relative intensity)]:
389 (35.0) [M?2], 387 (100) [Mꢀ?], 247 (14.5) [M–
ClC6H4CHO], 140 (7.8) [ClC6H4CHO]. Anal. Calcd. for
C21H23N2O3Cl: C, 65.20; H, 5.99; N, 7.24. Found: C, 64.67;
H, 5.58; N, 6.98.
1-(3-[3-{4-(4-Chlorobenzyl)piperazin-1-
yl}propoxy]phenyl)ethanone (9)
Yield 61.1 %. mp 282–285 °C. FTIR (KBr, cm-1): 3068,
2941, 1682, 1592, 1487, 1272, 1156, 1046, 1011, 956, 841,
1
791 and 688. H-NMR (400 MHz; CDCl3, d, J): 7.52 (dt,
1H, J = 7.7, 1.1 Hz); 7.48–7.45 (m, 1H); 7.35 (t, 1H,
J = 7.9 Hz); 7.27–7.25 (m, 4H); 7.10 (dd, 1H, J = 8.2,
2.6 Hz); 4.05 (t, 2H, J = 7.1 Hz); 3.47 (s, 2H), 2.59
(s, 3H), 2.55–2.49 (broadened m, 10H); 1.98 (quintet, 2H,
J = 7.1 Hz). MS [EI, m/z (relative intensity)]: 389 (40.0)
[M?2], 387 (100) [Mꢀ?], 261 (7.4) [M–(ClC6H4CH3], 125
(1.8) [ClC6H4CH2]. Anal. Calcd. for C22H27N2O2Cl: C,
68.29; H, 7.03; N, 7.24. Found: C, 67.68; H, 6.73; N, 6.98.
1-(3-[3-{4-(4-Chlorobenzoyl)piperazin-1-
yl}propoxy]phenyl)ethanone (13)
Yield 68.5 %. mp 296–298 °C. FTIR (KBr, cm-1): 3042,
2921, 1688, 1590, 1467, 1265, 1160, 1038, 1010, 950, 848,
123