piperazine, 8H), 3.40–3.54 (m, CH CH N (propyl (pyrrolidin-2-one), 50.3 (piperazine), 51.5 (CH CH N),
2
2
2
2
chain), CH CH CO (pyrrolidin-2-one), 4H), 3.57 (t, 52.6 (piperazine), 55.9 (CH ), 115.2, 115.3, 119.3,
2
2
3
NCH CH (propyl chain), 2H, J = 6.0 Hz), 3.75 (t, 122.0, 144.3, 145.5 (arom.), 173.4 (carbonyl).
2
2
CH CH N (pyrrolidin-2-one), 2H, J = 3.29 Hz), 6.96
2
2
–
7.18 (m, arom., 4H); 13C-NMR ([d ]-DMSO): d 15.8
6
(
CH ), 17.7 (CH CH CH (pyrrolidin-2-one), 24.9
3
1-{3-[4-(2-Ethoxy-phenyl)-piperazin-1-yl]-
propyl}-pyrrolidin-2-one dihydrochloride 13
2
2
2
(
CH CH CH (propyl chain)), 32.6 (CH CO (pyrro-
2
2
2
2
lidin-2-one)), 44.3 (NCH CH (propyl chain)), 46.4
2
2
(
CH CH CH (pyrrolidin-2-one), 50.3 (piperazine),
2 2 2
Yield: 39.4%. Anal. for C H N O 2HCl, calc. C
19 29 3 2
5
1
1.5 (CH CH N), 52.6 (piperazine), 114.2, 118.2,
2 2
5
7
6.43%, H 7.73%, N 10.39%, found 56.46%, H
27.0, 126.7, 127.0, 147.7 (arom.), 173.4 (carbonyl).
.80%, N 10.40%; M 404.37; m.p. 169.4–171.0°C;
r
1
TLC R = S (0.71), H-NMR ([d ]-DMSO): d 1.32 (t,
f
1
6
1-{3-[4-(2-Hydroxy-phenyl)-piperazin-1-yl]-
propyl}-pyrrolidin-2-one dihydrochloride 11
CH CH , 3H, J = 6.3 Hz), 2.18–2.28 (m, CH CH CH
2
3
2
2
2
(pyrrolidin-2-one), CH CH CH (propyl chain), 4H),
2 2 2
3
.01–3.26 (m, piperazine, 8H), 3.49–3.56 (m, CH CH N
2 2
Yield: 57.5%. Anal. for C H N O 2 HCl, calc. C
17 25 3 2
(propyl chain), CH CH CO (pyrrolidin-2-one), 4H),
2 2
54.26%, H 7.23%, N 11.17%, found C 54.30%, H.
3
.54 (t, NCH CH (propyl chain), 2H, J = 6.7 Hz),
2 2
7
.30%, N 11.20%; M 376.32; m.p. 209.8–211.3°C;
r
3
.64 (t, CH CH N (pyrrolidin-2-one), 2H, J = 3.7
2
2
1
TLC R = S (0.76), H-NMR ([d ]-DMSO): d 1.90–2.10
1
f
6
Hz), 4.02 (s, OCH , 2H, J = 6.3 Hz), 6.96–7.18 (m,
2
arom., 4H), 13C-NMR ([d ]-DMSO): d 14.8 (CH ),
(
m, CH CH CH CH CH CH (pyrrolidin-2-one), 4H),
2 2 2, 2 2 2
6
3
2.21–2.35 (m, CH CO (pyrrolidin-2-one), NCH CH
2 2 2
17.4 (CH CH CH (pyrrolidin-2-one), 24.9 (CH CH CH
2 2 2 2 2 2
(propyl chain), 4H), 2.69–2.74 (m, CH piper., 4H),
2
(propyl chain)), 32.6 (CH CO (pyrrolidin-2-one)),
2
2.85–2.99 (m, CH piper., 4H), 3.25 (dd, CH CH N
2 2 2
44.3 (NCH CH (propyl chain)), 46.4 (CH CH CH
2 2 2 2 2
(
propyl chain), 2H), 3.26 (s, OH, 1H), 3.43–3.58 (m,
(pyrrolidin-2-one), 50.3 (piperazine), 51.5 (CH CH N
2 2
CH CH N (pyrrolidin-2-one), 2H), 6.42–6.64 (m, arom.,
2
2
(propyl chain)), 52.6 (piperazine), 64.7 (CH ), 114.9,
2
H); 13C-NMR ([d ]-DMSO): d 17.7 (CH CH CH
4
6 2 2 2
115.3, 118.9, 121.3, 142.3, 144.4 (arom.), 173.4 (car-
(pyrrolidin-2-one), 24.9 (CH CH CH (propyl chain)),
2 2 2
bonyl).
32.6 (CH CO (pyrrolidin-2-one)), 44.3 (NCH CH
2 2 2
(propyl chain)), 46.4 (CH CH CH (pyrrolidin-2-one),
2 2 2
5
0.3 (piperazine), 51.5 (CH CH N), 52.6 (piperazine),
2 2
1-{3-[4-(3-Chloro-phenyl)-piperazin-1-yl]-
propyl}-pyrrolidin-2-one dihydrochloride 14
115.7, 116.8, 119.7, 122.3, 142.4, 145.9 (arom.),
1
73.4 (carbonyl).
Yield: 37.6%. Anal. for C H ClN O 2HCl, calc. C
24
17
3
1-{3-[4-(2-Methoxy-phenyl)-piperazin-1-yl]-
propyl}-pyrrolidin-2-one dihydrochloride 12
51.72%, H 6.64%, N 10.64%, found C 52.00%, H
6.68%, N 10.67%; M 394.77; m.p. 201.4°C (dec);
r
1
TLC R = S (0.81), H-NMR ([d ]-DMSO): d 2.20–2.32
6
Yield: 35.1%. Anal. for C H N O 2HCl, calc. C
f
1
1
8 27 3 2
(
(
m, CH CH CH (pyrrolidin-2-one), CH CH CH
2 2 2 2 2 2
5
5.38%, H 7.49%, N 10.76%, found C 55.42%, H
propyl chain), 4H), 3.10–3.28 (m, piperazine, 8H),
7.56%, N 10.76%; M 390.35; m.p. 195 °C (dec); TLC
r
1
3.38-3.48 (m, CH CH N (propyl chain), CH CH CO
2 2 2 2
R = S (0.65), H-NMR ([d ]-DMSO): d 2.20–2.29 (m,
f
1
6
(pyrrolidin-2-one), 4H), 3.61 (t, NCH CH (propyl
2 2
CH CH CH (pyrrolidin-2-one), CH CH CH (propyl
2
2
2
2
2
2
chain), 2H, J = 5.3 Hz), 3.89 (t, CH CH N (pyrro-
2
chain), 4H), 3.08–3.21 (m, piperazine, 8H), 3.43–3.54
m, CH CH N (propyl chain), CH CH CO (pyrroli-
2
lidin-2-one), 2H, J = 4.9 Hz), 7.12-7.30 (m, arom.,
din-2-one), 4H), 3.62 (t, NCH CH (propyl chain), 4H); 13C-NMR ([d6]-DMSO): d 17.7 (CH2CH2CH2
(
2
2
2
2
2
2
2
H, J = 5.8 Hz), 3.70 (s, OCH , 3H), 3.75 (t, (pyrrolidin-2-one), 25.0 (CH2CH2CH2 (propyl chain)),
3
CH CH N (pyrrolidin-2-one), 2H, J = 3.3 Hz), 6.86 32.6 (CH CO (pyrrolidin-2-one)), 44.3 (NCH CH
2
2
2
2
2
7.03 (m, arom., 4H); 13C-NMR ([d ]-DMSO): d 17.4 (propyl chain)), 46.4 (CH CH CH (pyrrolidin-2-
–
6
2 2 2
(
CH CH CH (pyrrolidin-2-one), 24.9 (CH CH CH
2
one), 50.0 (piperazine), 51.5 (CH CH N (propyl
2 2
2
2
2
2
2
(
propyl chain)), 32.6 (CH CO (pyrrolidin-2-one)), chain)), 52.6 (piperazine), 112.4, 114.7, 118.4, 131.1,
2
4
4.3 (NCH CH (propyl chain)), 46.4 (CH CH CH
2
135.2, 151.0 (arom.), 173.4 (carbonyl).
2
2
2
2
72