KOROLEVA et al.
1562
(1.5 mmol) of DCC was added, and the mixture was
stirred for 20 h. The product was isolated as described
above for amide XV (including evaporation of ethyl
acetate). Yield 80%, yellow liquid. IR spectrum (film),
NHCO). 13C NMR spectrum (CDCl3), δC, ppm: 25.31,
46.19, 52.89, 55.17, 62.10, 105.02, 115.24, 117.10,
119.01, 120.51, 127.39, 127.47, 130.19, 130.31,
130.59, 136.30, 141.86, 143.19, 148.92, 154.51,
156.83, 158.90, 169.11, 170.93. Mass spectrum, m/z
(Irel, %): 451 (35) [M]+, 99 (100) [MeN(CH2)4N]+.
Found, %: C 74.41; H 6.28; N 15.30. C28H29N5O. Cal-
culated, %: C 74.50; H 6.43; N 15.52.
1
ν, cm–1: 1720 (C=O), 1680 (CHO). H NMR spectrum
(CDCl3), δ, ppm: 2.32 s (3H, NMe); 2.35 br.s,
2.61 br.s, 2.94 br.s, 3.82 br.s [8H, N(CH2)4N]; 7.56 d,
3
7.93 d (4H, Harom, J = 7.9 Hz); 10.04 s (1H, CHO).
13C NMR spectrum (CDCl3), δC, ppm: 41.91, 45.87,
54.46, 55.06, 62.53, 127.67, 129.82, 136.79, 141.38,
168.79, 191.41. Mass spectrum, m/z (Irel, %): 232 (2)
[M]+, 105 (23) [C6H4CHO]+, 133 (30%) [M –
MeN(CH2)4N]+, 99 (28) [MeN(CH2)4N]+, 70 (90).
Found, %: C 66.95; H 6.72; N 11.88. C13H16N2O2. Cal-
culated, %: C 67.24; H 6.90; N 12.07.
Compound XIX. Yield 40%, mp 173–174°C. IR
spectrum (KBr), ν, cm–1: 3410, 3280 (NH), 1695
1
(C=O), 1580 (δNH). H NMR spectrum (CDCl3), δ,
ppm: 2.30 s (3H, NMe), 2.48–2.54 m [8H, N(CH2)4N],
2.72 s (3H, Me), 3.48 s (3H, CH2), 4.55 br.s (1H, NH);
6.48 d, 6.80 d, 7.12 m, 7.23 d, 7.42 d, 7.45 m, 7.54 d,
3
8.10 d, 8.68 d.d (13H, Harom, J = 8.0 Hz); 8.60 s (1H,
NHCO). 13C NMR spectrum (CDCl3), δC, ppm: 25.37,
43.17, 46.17, 53.16, 55.22, 62.46, 104.94, 115.12,
116.75, 118.66, 120.56, 127.46, 127.67, 129.01,
130.30, 130.38, 130.68, 136.35, 142.07, 143.15,
149.04, 154.49, 156.99, 158.86, 169.04, 171.19. Mass
spectrum, m/z (Irel, %): 465 (29) [M]+, 450 (10) [M –
Me]+, 99 (100) [MeN(CH2)4N]+. Found, %: C 74.60;
H 6.52; N 14.79. C29H31N5O. Calculated, %: C 74.84;
H 6.67; N 15.05.
4-(1H-Imidazol-1-yl)-N-[4-(4-Methylpiperazin-
1-ylmethyl)phenyl]benzamide (XVII). A solution of
0.17 g (0.5 mmol) of benzamide VI in 10 ml of
dioxane was heated to 80°C, 0.035 g (0.5 mmol) of
imidazole was added under stirring, and the mixture
was heated for 6 h at 100°C. After cooling, the precip-
itate was filtered off and washed with dioxane and
diethyl ether (3×20 ml). Yield 50%, mp 189–190°C.
IR spectrum (KBr), ν, cm–1: 3410 (NH), 1685 (C=O),
1
N-(3-Amino-4-methylphenyl)-4-(4-methylpiper-
azin-1-ylmethyl)benzamide (XX). Amide X, 1.69 g
(5 mmol), was dissolved in 10 ml of methanol, 5 mmol
of skeletal Raney nickel was added, and 10 mmol of
80% hydrazine hydrate was then added. The mixture
foamed up and turned colorless. It was stirred for
45 min at 50–60°C and for 1 h at room temperature
and filtered through a layer of celite, and the filtrate
was evaporated. Yield 84%, colorless oily substance.
IR spectrum (film), ν, cm–1: 3400–3350 (NH, NH2),
1580 (δNH). H NMR spectrum (CDCl3), δ, ppm:
2.35 s (3H, NMe), 2.56 br.s [8H, N(CH2)4N], 3.59 s
(3H, CH2); 6.28 d, 7.24 d, 7.49 d, 7.73 d, 8.11 d,
3
8.36 s, 8.81 d (11H, Harom, J = 8.1 Hz), 8.24 s (1H,
NH). 13C NMR spectrum (CDCl3), δC, ppm: 19.15,
46.01, 54.39, 62.47, 116.60, 119.41, 120.82, 126.13,
129.52, 129.70, 129.85, 140.74, 141.23, 143.14, 166.13.
Mass spectrum, m/z (Irel, %): 375 (18) [M]+, 99 (100)
[MeN(CH2)4N]+. Found, %: C 70.24; H 6.43; N 18.50.
C22H25N5O. Calculated, %: C 70.38; H 6.71; N 18.65.
1
1685 (C=O), 1600 (δNH). H NMR spectrum (CDCl3),
N-[4-(4-Methylpiperazin-1-ylmethyl)phenyl]-4-
[(quinolin-5-yl- and 2-methylquinolin-5-yl)amino]-
benzamides XVIII and XIX (general procedure).
A solution of equimolar amounts (0.5 mmol) of benz-
amide VI and quinolin-5-amine or 2-methylquinolin-
5-amine in 10 ml of dioxane was stirred for 30 h at
100°C. The precipitate was filtered off, washed with
dioxane and diethyl ether (3×20 ml), and recrystal-
lized from chloroform–hexane.
δ, ppm: 2.14 (3H, Me), 2.29 s (3H, MeN), 2.47 br.s
[8H, N(CH2)4N], 3.55 s (2H, CH2), 3.68 s (2H, NH2);
6.73 d.d, 6.99 d, 7.42 d, 7.88 d, 7.46 d, 7.92 s (7H,
3
4
Harom, J = 8.2, J = 2.0 Hz); 7.29 br.s (1H, NHCO).
13C NMR spectrum (CDCl3), δC, ppm: 16.85, 45.93,
53.01, 55.03, 62.47, 106.84, 110.08, 118.58, 126.92,
129.27, 130.59, 133.96, 136.89, 142.41, 145.12, 165.43.
Mass spectrum, m/z (Irel, %): 338 (27) [M]+, 323 (18)
[M – Me]+, 307 (15) [M – Me – NH2]+, 240 (30) [M –
MeN(CH2)4N + 1]+, 118 (8) [COC6H4CH2]+, 99 (100)
[MeN(CH2)4N]+. Found, %: C 70.71; H 7.55; N 16.39.
C20H26N4O. Calculated, %: C 70.98; H 7.74; N 16.55.
Compound XVIII. Yield 37%, mp 198–199°C. IR
spectrum (KBr), ν, cm–1: 3430, 3285 (NH), 1685
1
(C=O), 1590 (δNH). H NMR spectrum (CDCl3), δ,
ppm: 2.33 s (3H, NMe), 2.49 br.s [8H, N(CH2)4N],
3.53 s (3H, CH2), 4.39 s (1H, NH); 6.50 d, 6.79 d,
7.08 m, 7.21 d, 7.28 d, 7.41 d, 7.56 d, 8.22 d, 8.68 d.d
[4-(3-Amino-4-methylphenyaminomethyl)-
phenyl](4-methylpiperazin-1-yl)methanone (XXII)
was synthesized from nitro amide XV according to the
procedure described above for amide XX. Yield 77%,
3
4
(14H, Harom, J = 8.2, J = 4.0 Hz); 8.53 s (1H,
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 47 No. 10 2011