4
Journal of Chemistry
C
–H), 4.20 (s, 2H, –COCH ), 6.87 (d, 2H, ꢀ = 8.31 Hz,
1H-NMR (500 MHz, DMSO-d6): 1.23 (t, 6H, ꢀ = 7.18 Hz, –
2,6
2
phenyl, C –H), 7.40 (d, 2H, ꢀ = 8.39 Hz, phenyl, C –H),
N(CH CH ) ), 3.04 (q, 4H, ꢀ = 7.16 Hz, –N(CH CH ) ),
3,5
2,6
2
3 2
2
3 2
9.99 (s, 1H, –NHCO). MS (ESI) (m/z): [M + 1]+ 364.11. Anal.
3.39–3.49 (m, 4H, morpholine, C –H), 3.72–3.76 (m, 4H,
3,5
Calcd. for C H N OS : C, 59.47; H, 6.93; N, 11.56; Found:
morpholine, C –H), 4.19 (s, 2H, –COCH ), 6.89 (d, 2H,
18 25
3
2
2,6
2
C, 59.22; H, 6.91; N, 11.59.
ꢀ = 8.33 Hz, phenyl, C –H), 7.45 (d, 2H, ꢀ = 8.29 Hz, phenyl,
3,5
C
–H), 10.06 (s, 1H, –NHCO). MS (ESI) (m/z): [M + 1]+
2,6
368.12. Anal. Calcd. for C H N O S : C, 55.56; H, 6.86; N,
17 25
3
2
2
2.5.4. N-[4-(Piperidin-1-yl)phenyl]-2-(piperidin-1-yl-thiocarbon-
ylthio)acetamide (4d). IR (KBr) ]max (cm−1): 3287 (N–H),
1659 (C=O), 1234 (C=S), 822 (1,4-disubstituted benzene).
1H-NMR (500 MHz, DMSO-d6): 1.51–1.66 (m, 12H, 2 ×
piperidine, C –H), 3.04–3.08 (m, 4H, piperidine, C –H),
11.43; Found: C, 56.62; H, 6.85; N, 11.41.
2.5.9. N-[4-(Morpholin-4-yl)phenyl]-2-(pyrrolidin-1-yl-thiocar-
bonylthio)acetamide (4i). IR (KBr) ]max (cm−1): 3287 (N–H),
1659 (C=O), 1234 (C=S), 822 (1,4-disubstituted benzene). 1H-
NMR (500 MHz, DMSO-d6): 1.93–2.07 (m, 4H, pyrrolidine,
3,4,5
2,6
3.41–3.47 (m, 4H, piperidine, C –H), 4.20 (s, 2H, –COCH ),
2,6
2
6.87 (d, 2H, ꢀ = 8.36 Hz, phenyl, C –H), 7.40 (d, 2H, ꢀ =
3,5
8.29 Hz, phenyl, C –H), 10.01 (s, 1H, –NHCO). MS (ESI)
2,6
C
–H), 3.03–3.06 (m, 4H, pyrrolidine, C –H), 3.41–3.48
3,4
2,5
(m/z): [M + 1]+ 378.19. Anal. Calcd. for C H N OS : C,
(m, 4H, morpholine, C –H), 3.73–3.82 (m, 4H, morpholine,
19 27
3
2
3,5
60.44; H, 7.21; N, 11.13; Found: C, 60.70; H, 7.19; N, 11.15.
C
–H), 4.21 (s, 2H, –COCH ), 6.89 (d, 2H, ꢀ = 8.36 Hz,
2,6
2
phenyl, C –H), 7.44 (d, 2H, ꢀ = 8.31 Hz, phenyl, C –H),
3,5
2,6
10.05 (s, 1H, –NHCO). MS (ESI) (m/z): [M + 1]+ 336.17. Anal.
2.5.5. N-[4-(Piperidin-1-yl)phenyl]-2-(4-methylpiperidin-1-yl-
thiocarbonylthio)acetamide (4e). IR (KBr) ]max (cm−1): 3291
Calcd. for C H N O S : C, 55.86; H, 6.34; N, 11.50; Found:
17 23
3
2
2
C, 55.94; H, 6.37; N, 11.51.
(N–H), 1659 (C=O), 1234 (C=S), 822 (1,4-disubstituted ben-
1
zene). H-NMR (500 MHz, DMSO-d6): 0.93 (d, 3H, ꢀ =
7.11 Hz, –CH ), 1.50–1.64 (m, 11H, 2 × piperidine, C
–
3
3,4,5
2.5.10. N-[4-(Morpholin-4-yl)phenyl]-2-(piperidin-1-yl-thiocar-
bonylthio)acetamide (4j). IR (KBr) ]max (cm−1): 3289 (N–H),
1651 (C=O), 1217 (C=S), 821 (1,4-disubstituted benzene). 1H-
NMR (500 MHz, DMSO-d6): 1.56–1.64 (m, 6H, piperidine,
H), 3.04–3.09 (m, 4H, piperidine, C –H), 3.41–3.46 (m, 4H,
2,6
piperidine, C –H), 4.19 (s, 2H, –COCH ), 6.87 (d, 2H, ꢀ =
2,6
2
8.33 Hz, phenyl, C –H), 7.40 (d, 2H, ꢀ = 8.43 Hz, phenyl,
3,5
C
–H), 10.02 (s, 1H, –NHCO). MS (ESI) (m/z): [M + 1]+
2,6
C
–H), 3.03–3.06 (m, 4H, piperidine, C –H), 3.41–3.48
3,4,5
2,6
392.14. Anal. Calcd. for C H N OS : C, 61.34; H, 7.46; N,
20 29
3
2
(m, 4H, morpholine, C –H), 3.73–3.86 (m, 4H, morpholine,
3,5
10.73; Found: C, 61.42; H, 7.45; N, 10.70.
C
–H), 4.20 (s, 2H, –COCH ), 6.89 (d, 2H, ꢀ = 8.42 Hz,
2,6
2
phenyl, C –H), 7.44 (d, 2H, ꢀ = 8.38 Hz, phenyl, C –H),
3,5
2,6
10.05 (s, 1H, –NHCO). MS (ESI) (m/z): [M + 1]+ 380.15. Anal.
2.5.6. N-[4-(Piperidin-1-yl)phenyl]-2-(4-benzylpiperidin-1-yl-
thiocarbonylthio)acetamide (4f). IR (KBr) ]max (cm−1): 3289
(N–H), 1659 (C=O), 1234 (C=S), 822 (1,4-disubstituted ben-
Calcd. for C H N O S : C, 56.96; H, 6.64; N, 11.07; Found:
18 25
3
2
2
C, 57.10; H, 6.67; N, 11.08.
1
zene). H-NMR (500 MHz, DMSO-d6): 1.44–1.63 (m, 11H,
2 × piperidine, C –H), 2.54 (d, 2H, ꢀ
=
7.14 Hz,
3,4,5
2.5.11.N-[4-(Morpholin-4-yl)phenyl]-2-(4-methylpiperidin-1-yl-
thiocarbonylthio)acetamide (4k). IR (KBr) ]max (cm−1): 3288
(N–H), 1659 (C=O), 1234 (C=S), 822 (1,4-disubstituted ben-
–CH C H ), 3.04–3.10 (m, 4H, piperidine, C –H), 3.42–
2
6
5
2,6
3.48 (m, 4H, piperidine, C –H), 4.19 (s, 2H, –COCH ),
2,6
2
6.87 (d, 2H, ꢀ = 8.22 Hz, phenyl, C –H), 7.19–7.31 (m, 5H,
1
3,5
zene). H-NMR (500 MHz, DMSO-d6): 0.94 (d, 3H, ꢀ =
–CH C H ), 7.41 (d, 2H, ꢀ = 8.30 Hz, phenyl, C –H), 10.02
2
6
5
2,6
7.14 Hz, –CH ), 1.50–1.65 (m, 5H, piperidine, C –H),
3
3,4,5
(s, 1H, –NHCO). MS (ESI) (m/z): [M + 1]+ 468.17. Anal. Calcd.
3.03–3.09 (m, 4H, piperidine, C –H), 3.40–3.46 (m, 4H,
2,6
for C H N OS : C, 66.77; H, 7.11; N, 8.98; Found: C, 66.59;
26 33
3
2
morpholine, C –H), 3.71–3.77 (m, 4H, morpholine, C
–
3,5
2,6
H, 7.09; N, 9.00.
H), 4.19 (s, 2H, –COCH ), 6.88 (d, 2H, ꢀ = 8.31 Hz, phenyl,
2
C
–H), 7.42 (d, 2H, ꢀ = 8.39 Hz, phenyl, C –H), 10.02 (s,
3,5
2,6
1H, –NHCO). MS (ESI) (m/z): [M + 1]+ 394.18. Anal. Calcd.
2.5.7. N-[4-(Morpholin-4-yl)phenyl]-2-(dimethylaminothiocar-
bonylthio)acetamide (4g). IR (KBr) ]max (cm−1): 3287 (N–
H), 1659 (C=O), 1234 (C=S), 822 (1,4-disubstituted benzene).
for C H N O S : C, 57.98; H, 6.91; N, 10.68; Found: C, 58.08;
H, 6.92; N, 10.69.
19 27
3
2
2
1H-NMR (500 MHz, DMSO-d6): 3.04 (s, 6H, –N(CH ) ),
3 2
3.41–3.47 (m, 4H, morpholine, C –H), 3.72–3.74 (m, 4H,
3,5
2.5.12. N-[4-(Morpholin-4-yl)phenyl]-2-(4-benzylpiperidin-1-
yl-thiocarbonylthio)acetamide (4l). IR (KBr) ]max (cm−1):
3289 (N–H), 1659 (C=O), 1233 (C=S), 822 (1,4-disubstituted
benzene). 1H-NMR (500 MHz, DMSO-d6): 1.51–1.62 (m, 5H,
piperidine, C –H), 2.52 (d, 2H, ꢀ = 7.22 Hz, –CH C H ),
morpholine, C –H), 4.18 (s, 2H, –COCH ), 6.89 (d, 2H,
2,6
2
ꢀ = 8.32 Hz, phenyl, C –H), 7.44 (d, 2H, ꢀ = 8.44 Hz,
3,5
phenyl, C –H), 10.01 (s, 1H, –NHCO). MS (ESI) (m/z): [M +
2,6
1]+ 340.15. Anal. Calcd. for C H N OS : C, 53.07; H, 6.24;
15 21
3
2
3,4,5
2
6
5
N, 12.38; Found: C, 53.33; H, 6.25; N, 12.36.
3.05–3.08 (m, 4H, piperidine, C –H), 3.41–3.47 (m, 4H,
2,6
morpholine, C –H), 3.72–3.78 (m, 4H, morpholine, C
–
3,5
2,6
2.5.8. N-[4-(Morpholin-4-yl)phenyl]-2-(diethylaminothiocar-
bonylthio)acetamide (4h). IR (KBr) ]max (cm−1): 3289 (N–
H), 1659 (C=O), 1235 (C=S), 822 (1,4-disubstituted benzene).
H), 4.18 (s, 2H, –COCH ), 6.89 (d, 2H, ꢀ = 8.38 Hz, phenyl,
2
C
–H), 7.19–7.31 (m, 5H, –CH C H ), 7.41 (d, 2H, ꢀ =
3,5
2
6
5
8.43 Hz, phenyl, C –H), 10.04 (s, 1H, –NHCO). MS (ESI)
2,6