Molecular Diversity
2926.45 and 2795.31 (CH stretch of CH2), 1633.41 (C=O
stretch), 1536.02 (C=C stretch), 1241.93 (C–N stretch),
DMSO-d6) δ 7.27–2.22 (m, 2H; Ar–H); 7.20–7.16 (m, 3H,
Ar–H); 7.02 (t, J=5.54 Hz, 1H; NH), 6.83 (d, J=10.36 Hz,
2H; Ar–H), 6.73 (d, J=7.915 Hz, 1H; Ar–H), 5.97 (s, 2H;
O–CH2–O), 4.20 (d, J = 5.52 Hz, 2H; Bn CH2), 3.80 (d,
J=13.36 Hz, 1H; piperazine CH), 3.60 (dd, 2H, J=26.34,
12.63 Hz; CH2), 3.10 (d, J=13.24 Hz, 1H; piperazine CH),
2.90 (t, J = 10.10 Hz, 1H; piperazine CH), 2.73 (dd, 1H,
J = 12.59,8.28 Hz, piperazine CH), 2.55(s, overlapping
with DMSO, 1H), 2.49–2.39(m, 1H, piperazine CH), 1.96
(t, J = 9.42 Hz, 1H; piperazine CH), 1.03 (d, J= 6.00 Hz,
3H); positive ion HRMS (C21H25N3O3) calculated 368.1974
found 368.1977.
1
1036.55 (C–O stretch); H NMR (400 MHz, DMSO-d6) δ
7.29–7.15 (m, 5H; Ar–H), 6.88 (app. t, 1H; NH), 6.84–6.78
(m, 2H; Ar–H), 6.70 (d, J = 7.80 Hz, 1H; Ar–H), 5.96 (s,
2H; O–CH2–O), 4.20 (d, J=5.80 Hz, 2H; Bn CH2), 3.37 (s,
2H; piperonyl CH2), 3.34 (br.s, 2H; CH2), 2.8 (s, 3H; CH3),
2.42 (br.s, 2H; CH2), 2.09 (s, 3H; CH3); positive ion HRMS
(C20H25N3O3) calculated 356.1974 found 356.1941.
4‑[(Benzo[d] [1, 3] dioxol‑5‑yl)methyl]‑N‑ben‑
zyl‑2‑methylpiperazine‑1‑carboxamide (13)
The title compound was synthesized by following the gen-
eral procedure for synthesis of urea derivative (isolated
yield 45.2%); it was found by HPLC to be 96.39% pure; IR
(KBr): v/cm−1 =3469.31 (NH stretch), 2924.52 and 2811.7
(CH stretch of CH2), 1628.59 (C=O stretch), 1545.67 (C=C
stretch), 1449.24 (CH for CH3), 1252.54 (C–N stretch),
4‑[(Benzo[d] [1, 3] dioxol‑5‑yl)methyl]‑N‑ben‑
zyl‑2,6‑dimethylpiperazine‑1‑carboxamide (15)
The title compound was synthesized by following the gen-
eral procedure for synthesis of urea derivative. (Isolated
yield 74.31%); IR (KBr): v/cm−1 = 3225.36 (NH stretch),
2918.73 and 2879.2 (CH stretch of CH2), 1617.98 (C=O
stretch), 1536.02 (C=C stretch), 1400.07 (CH for CH3),
1
1035.59 (C–O stretch); H NMR (400 MHz, DMSO-d6) δ
7.28(t, 2H, J = 7.389 Hz, Ar–H), 7.16–7.24(m, 3H); 6.98
(t, J=5.70 Hz, 1H; NH), 6.84 (t, 2H, J=6.53 Hz; Ar–H),
6.74 (d, J=7.80 Hz, 1H; Ar–H), 5.97 (d, 2H, J =3.32 Hz,
O–CH2–O), 4.25 (overlapping dd, J=15.41, 5.78 Hz, 1H,
piperazine H), 4.18 (overlapping dd, J= 15.52, 5.75 Hz,
1H piperazine H); 4.11(br.s, 1H, piperazine CH); 3.70 (d,
J=12.72 Hz, 1H; piperazine H), 3.39(d, J=13.19 Hz, 1H
piperazine H); 3.28 (d, J = 13.216 Hz, 1H, piperazine H);
2.92 (td, J = 2.50, 12.35 Hz, 1H; piperazine H), 2.72 (d,
J=10.17 Hz, 1H; piperazine H), 2.56 (d, J=11.04 Hz, 1H;
piperazine H), 1.99 (dd, J=3.35, 10.98 Hz, 1H; piperazine
H), 1.86 (td, J=3.03, 11.82 Hz, 1H; piperazine H), 1.12 (d,
J=6.548 Hz, 3H; CH3); 13C NMR (400 MHz, DMSO-d6)
δ 158.05 (C=O), 157.01 (Ar CH), 147.23 (Ar CH), 146.11
(Ar CH), 141.16 (Ar CH), 140.88 (Ar CH) (Ar CH), 132.05
(Ar CH), 128.18 (Ar CH), 128.04 (Ar CH), 126.96 (Ar CH),
126.89 (Ar CH), 126.52 (Ar CH), 126.32 (Ar CH), 121.060
(Ar CH), 108.70 (Ar CH), 107.86 (Ar CH), 100.74 (O-CH2),
61.54 (CH2), 56.99 (CH & CH2), 52.75 (CH2), 46.09 (CH2),
43.38 (CH2), 42.95 (CH2), 15.37 (CH3); positive ion HRMS
(C21H25N3O3) calculated 368.1974 found 368.1996.
1
1242.9 (C–N stretch), 1042.34 (C–O stretch); H NMR
(400 MHz, DMSO-d6) δ 7.28(t, J = 7.42 Hz, 2H; Ar–H),
7.22–7.16 (m, 3H; Ar–H), 6.9–6.83 (m, 3H; Ar–H & NH),
6.78 (d, J =7.88 Hz, 1H; Ar–H), 5.98 (s, 2H; O–CH2–O),
4.24 (d, J = 5.56 Hz, 2H; Bn CH2), 4.01 (app.t, 2H; pip-
erazine CH2), 3.37 (s, 2H; piperonyl CH2), 2.60–2.57 (m,
2H; piperazine CH2), 2.02–1.98 (m, 2H; piperazine CH2),
1.19 (d, J = 6.59 Hz, 6H; CH3*2); positive ion HRMS
(C22H27N3O3) calculated 382.2131 found 382.2129.
4‑[(Benzo[d] [1, 3] dioxol‑5‑yl)methyl]‑N‑ben‑
zyl‑3,5‑dimethylpiperazine‑1‑carboxamide (16)
The title compound was synthesized by following the gen-
eral procedure for synthesis of urea derivative (isolated
yield 64.21%); it was found by HPLC to be 96.49% pure;
IR (KBr): v/cm−1 = 3433.64 (NH stretch), 2923.56 and
2852.2 (CH stretch of CH2), 1630.52 (C=O stretch), 1540.85
(C=C stretch), 1401.03 (CH for CH3), 1242.9 (C–N stretch),
1
1037.52 (C–O stretch); H NMR (400 MHz, DMSO-d6) δ
7.27 (t, J=7.4 Hz, 2H; Ar–H), 7.19–7.16 (m, 3H; Ar–H),
7.04 (t, J=5.28 Hz, 1H, NH), 6.89 (s, 1H; Ar–H), 6.83–6.76
(m, 2H; Ar–H), 5.95 (s, 2H; O–CH2–O), 4.21 (d, J=5.56 Hz,
2H; Bn CH2), 3.81–3.78 (m, 2H; piperazine CH*2), 3.63 (s,
2H; piperonyl CH2), 2.54 (br.s merged with DMSO, 2H;
piperazine CH2), 2.48 (br.s, 2H; piperazine CH2), 0.90 (d,
J=5.85 Hz, 6H; CH3*2); positive ion HRMS (C22H27N3O3)
calculated 382.2131 found 382.2143.
4‑[(Benzo[d] [1, 3] dioxol‑5‑yl)methyl]‑N‑ben‑
zyl‑3‑methylpiperazine‑1‑carboxamide (14)
The title compound was synthesized by following the
general procedure for synthesis of urea derivative (iso-
lated yield 57.71%); it was found by HPLC to be 98.62%
pure; IR (KBr): v/cm−1 = 3428.81 (NH stretch), 2919.7
and 2857.02 (CH stretch of CH2), 1622.8 (C=O stretch),
1559.17 (C=C stretch), 1498.42 (CH for CH3), 1267 (C–N
1
stretch), 1037.52 (C–O stretch); H NMR (400 MHz,
1 3