Synthesis of Novel 4-(Dimethylaminoalkyl)piperazine-1-carbodithioate
Letters in Drug Design & Discovery, 2017, Vol. 14, No. 5 531
56.80, 129.29, 130.30, 135.71, 138.52, 195.37, 198.72.HRMS
(m/z): [M+H]+ calculated for C19H28N3OS2Cl: 414.1435;
found 414.1423.
192.95, 194.65.HRMS (m/z): [M+H]+ calculated for
C18H26N4O3S2: 411.1519; found411.1508.
2-(4-cyanophenyl)-2-oxoethyl 4-(3-(dimethylamino)propyl)
piperazine-1-carbodithioate (4e)
2-phenyl-2-oxoethyl 4-(3-(dimethylamino)propyl)piper-azine-1-
carbodithioate (4a)
Yields: 86%. M.P: 84.4-85.1°C. FTIR (ATR) cm-1: 2228
Yields: 87%. M.P: Oil. FTIR (ATR) cm-1: 1685 (C=O),
1224 (C=S), 753, 687 (monosubstituted benzene).1H-NMR
(500 MHz, DMSO-d6): δ = 1.53 (2H, p, J=7.50 Hz, -CH2-),
2.18 (6H, s, -CH3), 2.26 (2H, t, J=7.50 Hz, -CH2-), 2.36 (2H,
t, J=7.50 Hz, -CH2-), 2.45 (4H, s, piperazine CH2), 4.02 (2H,
s, piperazine CH2), 4.17 (2H, s, piperazine -CH2-), 4.96 (2H,
s, -CH2-), 7.55 (2H, t, J=7.60 Hz, –CH-), 7.69 (1H, t, J=7.60
Hz, –CH-), 8.02 (2H, d, J=7.60 Hz, –CH-).13C-NMR (125
MHz, DMSO-d6): δ = 24.57, 45.56, 46.77, 50.23, 52.13,
53.02, 55.72, 57.65, 128.86, 129.31, 133.68, 136.55, 193.32,
194.69.HRMS (m/z): [M+H]+ calculated for C18H27N3OS2:
366.1668; found 366.1654.
(CN), 1694 (C=O), 1236 (C=S), 826 (1,4-disubstituted ben-
1
zene). H-NMR (500 MHz, DMSO-d6): δ = 1.56 (2H, p,
J=7.40 Hz, -CH2-), 2.16 (6H, s, -CH3), 2.23 (2H, t, J=7.40
Hz, -CH2-), 2.35 (2H, t, J=7.40 Hz, -CH2-), 2.46 (4H, s,
piperazine CH2), 3.99 (2H, s, piperazine CH2), 4.19 (2H, s,
piperazine -CH2-), 4.96 (2H, s, -CH2-), 8.03 (2H, d, J=8.10
Hz, –CH-), 8.21 (2H, d, J=8.10 Hz, –CH-). 13C-NMR (125
MHz, DMSO-d6): δ = 23.34, 44.13, 45.58, 50.79, 51.94,
52.83, 55.65, 56.97, 115.48, 118.08, 129.77, 133.82, 140.23,
193.19, 194.83.HRMS (m/z): [M+H]+ calculated for C19H26
N4OS2: 391.1621; found 391.1605.
2-(4-bromophenyl)-2-oxoethyl 4-(3-(dimethylamino)propyl)
piperazine-1-carbodithioate (4f)
2-(4-methyl)-2-oxoethyl 4-(3-(dimethylamino)propyl)piper-
azine-1-carbodithioate (4b)
Yields: 82%. M.P: 108.6-109.2°C. FTIR (ATR) cm-1:
1684 (C=O), 1227 (C=S), 808 (1,4-disubstituted benzene).
1H-NMR (500 MHz, DMSO-d6): δ= 1.58 (2H, p, J=7.30 Hz,
-CH2-), 2.14 (6H, s, -CH3), 2.23 (2H, t, J=7.30 Hz, -CH2-),
2.34 (2H, t, J=7.30 Hz, -CH2-), 2.47 (4H, s, piperazine CH2),
3.99 (2H, s, piperazine CH2), 4.18 (2H, s, piperazine -CH2-),
4.93 (2H, s, -CH2-), 7.78 (2H, d, J=8.40 Hz, –CH-), 7.98
(2H, d, J=8.40 Hz, –CH-). 13C-NMR (125 MHz, DMSO-d6):
δ = 21.40, 43.93, 45.83, 50.46, 51.92, 52.76, 55.77, 57.60,
127.92, 130.67, 132.33, 135.85, 192.73, 194.59.HRMS
(m/z): [M+H]+ calculated for C18H26N3OS2Br: 444.0773;
found444.0760.
Yields: 77%. M.P: 153.9-154.5°C. FTIR (ATR) cm-1:
1690 (C=O), 1221 (C=S), 806 (1,4-disubstituted benzene).
1H-NMR (500 MHz, DMSO-d6): δ = 1.57 (2H, p, J=7.60 Hz,
-CH2-), 2.18 (6H, s, -CH3), 2.27 (2H, t, J=7.60 Hz, -CH2-),
2.35-2.42 (5H, m, -CH2-, -CH3), 2.46 (4H, s, piperazine
CH2), 3.98 (2H, s, piperazine CH2), 4.19 (2H, s, piperazine -
CH2-), 4.97 (2H, s, -CH2-), 7.35 (2H, d, J=8.00 Hz, –CH-),
7.97 (2H, d, J=8.00 Hz, –CH-).13C-NMR (125 MHz, DMSO-
d6): δ = 21.62, 24.65, 45.32, 46.82, 50.14, 52.03, 53.12,
55.84, 57.68, 128.19, 129.87, 134.21, 144.10, 192.57,
194.65.HRMS (m/z): [M+H]+ calculated for C19H29N3OS2:
380.1825; found 380.1811.
2-(4-fluorophenyl)-2-oxoethyl 4-(3-(dimethylamino)propyl)
piperazine-1-carbodithioate (4g)
2-(4-chlorophenyl)-2-oxoethyl 4-(3-(dimethylamino)propyl)
piperazine-1-carbodithioate (4c)
Yields: 79%. M.P: 78.2-78.9°C. FTIR (ATR) cm-1: 1685
(C=O), 1230 (C=S), 817 (1,4-disubstituted benzene). 1H-
NMR (500 MHz, DMSO-d6): δ = 1.57 (2H, p, J=7.30 Hz, -
CH2-), 2.16 (6H, s, -CH3), 2.26 (2H, t, J=7.30 Hz, -CH2-),
2.32 (2H, t, J=7.30 Hz, -CH2-), 2.46 (4H, s, piperazine CH2),
4.02 (2H, s, piperazine CH2), 4.20 (2H, s, piperazine -CH2-),
4.96 (2H, s, -CH2-), 7.39-7.70 (2H, m, –CH-), 8.11-8.16 (2H,
m, –CH-).13C-NMR (125 MHz, DMSO-d6): δ = 23.43,
44.12, 45.68, 50.43, 51.82, 52.67, 55.88, 56.75, 116.32 (d,
J=22.13 Hz), 131.65 (d, J=9.48 Hz), 133.54 (d, J=2.65 Hz),
165.57 (d, J=252.12 Hz), 192.14, 194.78.HRMS (m/z):
[M+H]+ calculated for C18H26N3OS2F: 384.1574; found
384.1583.
Yields: 82%. M.P: 120.7-121.4°C. FTIR (ATR) cm-1:
1692 (C=O), 1234 (C=S), 812 (1,4-disubstituted benzene).
1H-NMR (500 MHz, DMSO-d6): δ = 1.57 (2H, p, J=7.30 Hz,
-CH2-), 2.18 (6H, s, -CH3), 2.87 (2H, t, J=7.30 Hz, -CH2-),
2.36 (2H, m, J=7.30 Hz, -CH2-), 2.47 (4H, s, piperazine
CH2), 3.99 (2H, s, piperazine CH2), 4.19 (2H, s, piperazine -
CH2-), 4.86 (2H, s, -CH2-), 8.23 (2H, d, J=8.20 Hz, –CH-),
8.42 (2H, d, J=8.20 Hz, –CH-).13C-NMR (125 MHz, DMSO-
d6): δ = 24.54, 44.36, 45.27, 50.41, 51.85, 52.68, 55.57,
57.06, 129.59, 130.36, 135.21, 138.19, 192.68, 194.43.
HRMS (m/z): [M+H]+ calculated for C18H26N3OS2Cl: 400.
1279; found 400.1273.
2-(4-nitrophenyl)-2-oxoethyl 4-(3-(dimethylamino)propyl)
piperazine-1-carbodithioate (4d)
2-(2,4-difluorophenyl)-2-oxoethyl 4-(3-(dimethylamino) propyl)
piperazine-1-carbodithioate (4h)
Yields: 83%. M.P: 180.8-181.4°C. FTIR (ATR) cm-1:
Yields: 76%. M.P: 82.0-82.9°C. FTIR (ATR) cm-1:
1695 (C=O), 1522, 1344 (NO2), 1233 (C=S), 854 (1,4-
1686 (C=O), 1227 (C=S), 855, 808 (1,2,4-trisubstituted ben-
1
1
disubstituted benzene). H-NMR (500 MHz, DMSO-d6): δ =
zene). H-NMR (500 MHz, DMSO-d6): δ = 1.58 (2H, p,
1.84 (2H, p, J=7.60 Hz, -CH2-), 2.43 (2H, t, J=7.60 Hz, -
CH2-), 2.52 (4H, s, piperazine CH2), 2.79 (6H, s, -CH3), 3.18
(2H, t, J=7.60 Hz, -CH2-), 4.01 (2H, s, piperazine CH2), 4.19
(2H, s, piperazine -CH2-), 4.99 (2H, s, -CH2-), 8.28 (2H, d,
J=8.80 Hz, –CH-), 8.38 (2H, d, J=8.80 Hz, –CH-). 13C-NMR
(125 MHz, DMSO-d6): δ = 24.85, 44.10, 46.33, 50.42,
51.86, 52.45, 54.29, 55.88, 124.38, 130.03, 141.66, 150.42,
J=7.40 Hz, -CH2-), 2.16 (6H, s, -CH3), 2.25 (2H, t, J=7.40
Hz, -CH2-), 2.33 (2H, t, J=7.40 Hz, -CH2-), 2.46 (4H, s,
piperazine CH2), 3.97 (2H, s, piperazine CH2), 4.18 (2H, s,
piperazine -CH2-), 4.83 (2H, s, -CH2-), 7.26-7.29 (1H, m,
–CH-), 7.45-7.49 (1H, m, –CH-), 7.94-7.99 (1H, m,
–CH-).13C-NMR (125 MHz, DMSO-d6): δ = 24.77, 45.34,
46.88, 50.52, 51.99, 52.81, 55.73, 57.56, 105.70 (t, J=26.73