NEW 5-HT
3
RECEPTOR ANTAGONISTS
99
ꢀ
� 1
2
(
(
53 C (methanol±ether); IR (cm ): 2350
3Á38 (m, 10H, methylenes); 3Á21 (t, 2H, CH ); 1Á49
2
�
NHCl ); 1620 (C O); 1605 (arom.); 1495
(t, 3H, CH ).
3
1
C� N); 1245, 1035 (Ar� O� CH ). H NMR (d -
3
6
DMSO): 7Á20±6Á91 (m, 8H, Ar� H); 4Á49 (bs, 10H,
1-(1-Ethyl-1H-3-indolyl)-3-[4-(4-¯uorophenyl)
piperazin-1-yl]-1-propanone (10d). Yield 53%;
methylenes); 3Á770 (d, 2H, CH ); 3Á44 (s, 3H,
2
ꢀ
� 1
Ar� O� CH ); 3Á32 (s, 3H, CH ).
3
3
mp 227 C (methanol±ether); IR (cm ): 2350
�
(
(
NHCl ); 1630 (C O); 1590 (arom.); 1510
1
C� N); 1720(C� F). H NMR (d -DMSO): 8Á49±
1-(1-Methyl-1H-3-indolyl)-3-[4-(3-tri¯uoromethyl-
phenyl)piperazin-1-yl]-1-propanone (9h). Yield
9%; mp 224 C (methanol±ether); IR (cm ):
6
6
Á15 (m, 9H, Ar� H); 4Á64 (q, 2H, NCH ); 3Á91±
2
ꢀ
� 1
2
Á44 (m, 12H, methylenes); 1Á23 (t, 3H, CH ).
4
2
(
3
�
485 ( NHCl ); 1660 (C O); 1600 (arom.); 1495
1
C� N); 1120(C� F3). H NMR (d -DMSO): 8Á13±
6
1-(1-Ethyl-1H-3-indolyl)-3-[4-(2-methoxy phenyl)
piperazin-1-yl]-1-propanone (10e). Yield 59%;
7
Á33 (m, 9H, Ar� H); 3Á23±3Á03 (m, 10H, methy-
ꢀ
�
1
mp 217 C (methanol±ether); IR (cm ): 2475
(
lenes); 2Á63 (d, 2H, CH ); 1Á57 (t, 3H, CH ).
2
3
�
NHCl ); 1640 (C O); 1603 (arom.); 1520,
1
). H NMR (d
1-(1-Methyl-1H-3-indolyl)-3-[4-(2-pyridyl) piper-
azin-1-yl]-1-propanone (9i). Yield 68%; mp
1180 (C� N); 1260 (Ar� O� CH
3
6
-
DMSO): 8Á26±7Á06 (m, 9H, Ar� H); 4Á22 (q, 2H,
NCH
); 3Á63±3Á23 (m, 10H, methylenes); 3Á15 (s,
3H, Ar� O� CH ); 2Á72 (t, 2H, CH ); 1Á62 (t, 3H,
CH ).
ꢀ
� 1
2
(
58 C (methanol±ether); IR (cm ): 2425
NHCl ); 1655 (C O); 1595 (arom.); 1525,
2
�
3
2
1
1
7
510 (C N); 1180 (C� N). H NMR (D O): 8Á16-
3
2
Á11 (m, 9H, Ar� H); 4Á8±3Á47 (m, 12H, methy-
lenes); 2Á21 (s, 3H, CH ).
3
1-(1-Ethyl-1H-3-indolyl)-3-[4-(3-methoxyphenyl)
piperazin-1-yl]-1-propanone (10f). Yield 58%;
ꢀ
� 1
1
-(1-Methyl-1H-3-indolyl)-3-[4-(2-pyrimidinyl)
piperazin-1-yl]-1-propanone (9j). Yield 61%; mp
mp 111 C (ethanol±petroleum ether); IR (cm ):
1640 (C O); 1603 (arom.); 1520, 1180 (C� N);
ꢀ
� 1
1
). H NMR (CDCl
2
(
25 C (methanol±ether); IR (cm ): 2475
1260 (Ar� O� CH
3
3
): 8Á18±6Á97
�
NHCl ); 1655 (C O); 1595 (arom.); 1530,
(m, 9H, Ar� H); 4Á36 (q, 2H, NCH
10H, methylenes); 3Á20 (s, 3H, Ar� O� CH
2H, CH ).
); 1Á49 (t, 3H, CH
2
); 3Á83±3Á37 (m,
1
1
6
520 (C N); 1160(C� N). H NMR (D O): 8Á39±
3
); 2Á5 (t,
2
Á79 (m, 8H, Ar� H); 3Á99±3Á32 (m, 12H, methy-
2
3
lenes); 2Á20 (s, 3H, CH ).
3
1-(1-Ethyl-1H-3-indolyl)-3-[4-(4-methoxy phenyl)
piperazin-1-yl]-1-propanone (10g). Yield 60%;
1
1
(
1
-(1-Ethyl-1H-3-indolyl)-3-(4-phenyl piperazin-
ꢀ
-yl)-1-propanone (10a). Yield 49%; mp 201 C
methanol±ether); IR (cm ): 2510 ( NHCl );
ꢀ
� 1
mp 251 C (methanol±ether); IR (cm ): 2325
(
�
1
�
�
NHCl ); 1640 (C O); 1600 (arom.); 1510,
1
655 (C O); 1600 (arom.); 1160 (C� N).
H
1
1
040 (C� N); 1200 (Ar� O� CH ). H NMR (d -
3
6
NMR (d -DMSO): 7Á65±6Á84 (m, 10H, Ar� H);
6
DMSO): 8Á19±6Á87 (m, 9H, Ar� H); 4Á37 (q, 2H,
4
Á37 (q, 2H, NCH ); 3Á93±2Á51 (m, 12H, methy-
2
NCH ); 3Á84±3Á54 (m, 10H, methylenes); 3Á33 (s,
2
lenes); 1Á49 (q, 3H, CH ).
3
3
H, Ar� O� CH ); 2Á51 (t, 2H, CH ); 1Á49 (t, 3H,
3
2
CH ).
3
3
-[4-(3-Chlorophenyl)piperazin-1-yl]-1-(1-ethyl-
1
2
(
H-3-indolyl)-1-propanone (10b). Yield 55%; mp
ꢀ
� 1
1-(1-Ethyl-1H-3-indolyl)-3-[4-(3-tri¯uoromethyl-
phenyl)piperazin-1-yl]-1-propanone (10h). Yield
02 C (methanol±ether); IR (cm ): 2505
NHCl ); 1660 (C O); 1600 (arom.); 1495
�
ꢀ
� 1
68%; mp 218 C (methanol±ether); IR (cm ):
1
(
6
C� N); 1040 (C� Cl). H NMR (d -DMSO): 7Á65±
6
�
2
1
525 ( NHCl ); 1640 (C O); 1595 (arom.);
Á84 (m, 9H, Ar� H); 4Á02 (q, 2H, NCH ); 3Á46±
2
1
520, 1070 (C� N); 1120 (CF ). H NMR (d -
3
6
3
Á14 (m, 10H, methylenes); 2Á51 (s, 2H, CH ); 1Á45
2
DMSO): 8Á23±7Á13 (m, 9H, Ar� H); 4Á37 (q, 2H,
(t, 3H, CH ).
3
NCH ); 3Á55±3Á20 (m, 10H, methylenes); 2Á52 (d,
2
2
H, CH ); 1Á49 (t, 3H, CH ).
2
3
3
-[4-(4-Chlorophenyl)piperazin-1-yl]-1-(1-ethyl-
1
2
(
H-3-indolyl)-1-propanone (10c). Yield 51%; mp
ꢀ
� 1
20 C (methanol±ether); IR (cm ): 2435
NHCl ); 1630 (C O); 1595 (arom.); 1520
1-(1-Ethyl-1H-3-indolyl)-3-[4-(2-pyridyl) piper-
azin-1-yl]-1-propanone (10i). Yield 51%; mp
�
1
ꢀ
� 1
259 C (methanol±ether); IR (cm ): 2550
(C� N); 1020 (C� Cl). H NMR (d -DMSO): 8Á22±
6
�
6
Á59 (m, 9H, Ar� H); 4Á36 (q, 2H, NCH ); 3Á58±
( NHCl ); 1637 (C O); 1600 (arom.); 1540,
2
1
1520 (C N); 1140 (C� N). H NMR (d -DMSO):
6