Molecules 2019, 24, 497
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(E)-1-(Naphthalen-1-yl)-N-(phenyl(piperazin-1-yl)methylene)methanamine hydrochloride (II-1): Yield 34%,
Mp: 187–189 ◦C. 1H-NMR (400 MHz, D2O):
3.33 (t, 2H, J = 5.4 Hz, piperazinyl-H), 3.54–3.68 (m, 4H,
δ
piperazinyl-H), 4.12 (t, 2H, J = 5.4 Hz, piperazinyl-H), 4.82 (s, 2H, -CH2-), 7.22 (d, 1H, J = 7.2 Hz, ArH),
7.40–7.44 (m, 3H, ArH), 7.51–7.57 (m, 4H, ArH), 7.60–7.68 (m, 2H, ArH), 7.87 (d, 1H, J = 8.1 Hz, ArH),
7.87 (d, 1H, J = 9.0 Hz, ArH). HRMS calcd for C22H23N3 (M + H)+, 330.1965; found, 330.1962.
(E)-1-(Naphthalen-1-yl)-N-((4-nitrophenyl)(piperazin-1-yl)methylene)methanamine hydrochloride (II-2):
◦
1
Yield 11%, Mp: 202–204 C. H-NMR (400 MHz, D2O):
δ 3.34 (br, 2H, piperazinyl-H), 3.60 (br,
4H, piperazinyl-H), 4.21 (br, 2H, piperazinyl-H), 4.84 (s, 2H, -CH2-), 7.20 (d, 1H, J = 6.9 Hz, ArH),
7.38–7.43 (m, 1H, ArH), 7.46–7.53 (m, 2H, ArH), 7.56–7.61 (m, 3H, ArH), 7.84–7.89 (m, 2H, ArH), 8.17 (d,
2H, J = 9.0 Hz, ArH). HRMS calcd for C22H22N4O2 (M + H)+, 375.1816; found, 375.1814.
(E)-N-((4-Fluorophenyl)(piperazin-1-yl)methylene)-1-(naphthalen-1-yl)methanamine hydrochloride (II-3):
◦
1
Yield 24%, Mp: 193–195 C. H-NMR (400 MHz, D2O):
δ 3.36 (br, 2H, piperazinyl-H), 3.58 (br,2H,
piperazinyl-H), 3.65 (t, 2H, J = 4.2 Hz, J = 5.7 Hz, piperazinyl-H), 4.12 (t, 2H, J = 5.1 Hz, J = 5.4 Hz,
piperazinyl-H), 4.87 (s, 2H, -CH2-), 7.22–7.28 (m, 3H, ArH), 7.41–7.48 (m, 3H, ArH), 7.52–7.60 (m, 2H,
ArH), 7.65–7.68 (m, 1H, ArH), 7.91 (d, 1H, J = 8.4 Hz, ArH), 7.95–7.98 (m, 1H, ArH). HRMS calcd for
C22H22FN3 (M + H)+, 348.1871; found, 348.1873.
(E)-N-((2-Fluorophenyl)(piperazin-1-yl)methylene)-1-(naphthalen-1-yl)methanamine hydrochloride (II-4):
◦
1
Yield 41%, Mp: 148–150 C. H-NMR (400 MHz, D2O):
δ 3.33 (br, 2H, piperazinyl-H), 3.56 (br,2H,
piperazinyl-H), 3.67 (br, 2H, piperazinyl-H), 4.12–4.21 (m, 2H, piperazinyl-H), 4.92 (s, 2H, -CH2-),
7.12 (br, 1H, ArH), 7.23–7.29 (m, 1H, ArH), 7.33–7.46 (m, 3H, ArH), 7.56 (br, 2H, ArH), 7.64–7.72 (m,
2H, ArH), 7.88–8.05 (m, 2H, ArH). HRMS calcd for C22H22FN3 (M + H)+, 348.1871; found, 348.1868.
(E)-N-((2-Chlorophenyl)(pip◦erazin-1-yl)methylene)-1-(naphthalen-1-yl)methanamine hydrochloride (II-5):
1
Yield 58%, Mp: 165–167 C. H-NMR (400 MHz, D2O):
δ
3.34 (br, 2H, piperazinyl-H), 3.63 (br,
4H, piperazinyl-H), 4.15 (br, 2H, piperazinyl-H), 4.89 (s, 2H, -CH2-), 7.07 (d, 1H, J = 6.6 Hz, ArH),
7.37–7.49 (m, 3H, ArH), 7.55–7.65 (m, 4H, ArH), 7.78–7.81 (m, 1H, ArH), 7.91 (d, 1H, J = 8.7 Hz, ArH),
7.98–8.04 (m, 1H, ArH). HRMS calcd for C22H22ClN3 (M + H)+, 364.1575; found, 364.1574.
(E)-N-((3-Chlorophenyl)(pi◦perazin-1-yl)methylene)-1-(naphthalen-1-yl)methanamine hydrochloride (II-6):
1
Yield 34%, Mp: 198–200 C. H-NMR (400 MHz, D2O):
δ 3.31 (br, 2H, piperazinyl-H), 3.65 (br,4H,
piperazinyl-H), 4.12 (br, 2H, piperazinyl-H), 4.78 (s, 2H, -CH2-),7.16 (d, 1H, J = 6.9 Hz, ArH),
7.29–7.32 (m, 2H, ArH), 7.39–7.62 (m, 6H, ArH), 7.87 (d, 1H, J = 8.4 Hz, ArH), 7.93 (d, 1H, J = 6.9 Hz,
ArH). HRMS calcd for C22H22ClN3 (M + H)+, 364.1575; found, 364.1576.
(E)-N-((4-Chlorophenyl)(piperazin-1-yl)methylene)-1-(naphthalen-1-yl)methanamine hydrochloride (II-7):
1
Yield 41%, Mp: 210–212 ◦C. H-NMR (400 MHz, D2O):
δ 3.19 (t, 2H, J = 5.1 Hz, J = 5.1 Hz,
piperazinyl-H), 3.43 (t, 2H, J = 6.9 Hz, J = 3.9 Hz, piperazinyl-H), 3.50 (t, 2H, J = 5.7 Hz, piperazinyl-H),
4.12 (t, 2H, J = 6.0 Hz, piperazinyl-H), 4.75 (s, 2H, -CH2-), 7.09 (d, 1H, J = 6.6 Hz, ArH), 7.20 (d,
2H, J = 8.4 Hz, ArH), 7.30–7.35 (m, 1H, ArH), 7.38 (d, 2H, J = 8.4 Hz, ArH), 7.41–7.54 (m, 3H, ArH),
7.76–7.85 (m, 2H, ArH). HRMS calcd for C22H22ClN3 (M + H)+, 364.1575; found, 364.1577.
(E)-4-(((Naphthalen-1-ylmethyl)imino)(piperazin-1-yl)methyl)benzonitrile hydrochloride (II-8): Yield 30%,
◦
Mp: 158–160 C. 1H-NMR (400 MHz, D2O):
δ 3.34 (br, 2H, piperazinyl-H), 3.63 (br,4H, piperazinyl-H),
4.18 (br, 2H, piperazinyl-H), 4.84 (s, 2H, -CH2-), 7.19 (d, 1H, J = 7.2 Hz, ArH), 7.40–7.63 (m, 6H, ArH),
7.77 (d, 2H, J = 8.4 Hz, ArH), 7.88 (d, 1H, J = 8.1 Hz, ArH), 7.94 (d, 1H, J = 9.0 Hz, ArH). HRMS calcd
for C23H22N4 (M + H)+, 355.1917; found, 355.1921.