SYNTHESIS AND ESTIMATION OF ANTIBACTERIAL ACTIVITY
1205
NO3·HCl. Calculated, %: C 71.09; H 8.98; N 2.86; Cl
7.25.
CH3), 0.79–1.40 m (2Н, СН2), 0.98 d (6Н, СН3, J
6.6 Hz), 1.65 q (2Н, СН2, J 6.6 Hz), 1.76–1.92 t (1H,
CH), 1.79–1.95 m (2Н, СН2), 1.81 m (2Н, CH2), 3.93 t
(2Н, OCH2, J 6.6 Hz), 2.63 m (1H), 2.97–3.16 m [3Н,
N(CH2)2], 3.68–3.90 m [5Н, O(CH2)2, СН], 5.18 br
(1Н, ОН), 6.63 d (2H, J 8.9 Hz), 6.80–6.87 m (4H),
7.14–7.18 m (3H, 9Harom), 11.77 br (1Н, HCI). Found,
%: C 70.63; H 8.82; N 2.91; Cl 7.43. C28 H41NO3·HCl.
Calculated, %: C 70.66; Н 8.83; N 2.94; Cl 7.46.
3-(4-Butoxyphenyl)-1-(morpholin-4-yl)-2-
phenyldecan-3-ol hydrochloride (VId). Yield 69%,
mp 172–173oC, Rf 0.64. IR spectrum, ν, cm–1: 3340
1
(О–Н). Н NMR spectrum, δ, ppm: 0.84 t (3Н, СН3, J
6.8 Hz), 1.00 t (3Н, СН3, J 7.3), 0.81 br (1H) and 1.37
br (1H, CH2), 1.14–1.28 br (8H, CH2), 1.50 br.sextet
(2H, CH2, J 7.3 Hz), 1.74 m (2H, CH2), 1.82 br.m (2Н,
CH2), 2.63 br (1Н), 3.05 br [3Н, N(СН2)2], 3.42 br
(1Н, J 12.0 Hz), 3.71 br (1Н, CH2, J 12.0 Hz), 3.84 br
[4Н, О(CH2)2], 3.91 t (2Н, ОCH2, J 6.4 Hz), 4.01 br
(1Н, CH), 5.12 br (1Н, OH), 6.64 d (2Н, J 8.8 Hz),
6.84 br.d (2Н, J 8.8 Hz), 6.85 m (2Н), 7.15–7.19 m
(3Н, 9Н aryl), 11.92 br (1Н, HCI). Found, %: C 71.47;
H 9.13; N 2.76; Cl 9.14. C30 H45 NO3·HCl. Calculated,
%: C 71.49; H 9.13; N 2.78; Cl 7.05.
6-Methyl-3-[4-(3-methylbutoxy)phenyl]-1-
(morpholin-4-yl)-2-phenylheptan-3-ol hydrochlo-
ride (VIi). Yield 77%, mp 231–232oC, Rf 0.64. IR
1
spectrum, ν, cm–1: 3345 (О–Н). Н NMR spectrum, δ,
ppm: 0.62 d (3H, CH3, J 6.7 Hz), 0.93 d ((3Н, CH3, J
6.6 Hz), 0.98 d (6Н, 2СН3, J 6.6 Hz), 1.49 m (1Н,
СН), 1.65 q (2Н, СН2, J 6.6 Hz), 1.76–1.92 t (3H,
CH2, CH), 1.79–1.95 m (2Н, СН2), 2.66 br (1Н), 2.96–
3.15 m (2H ), 3.45 br.d (1Н, N(CH2)2, J 11.7 Hz),
3.68–3.90 m [6Н, O(CH2)2, СН2], 3.93 t (2H, OCH2, J
6.6 Hz), 4.03 m (1Н, CH), 5.17 br (1Н, ОН ), 6.64 d
(2H, J 8.9 Hz), 6.81–6.88 m (4H), 7.14–7.18 m (3H,
9Harom), 11.73 br (1Н, HCI). Found, %: C 71.04; H
8.97; N 2.85; Cl 7.14. C29 H43 NO3·HCl. Calculated, %:
C 71.09; Н 8.98; N 2.86; Cl 7.25.
1-(4-Butoxyphenyl)-1-(2-methoxyphenyl)-3-(mo-
rpholin-4-yl)-2-phenylpropan-3-ol hydrochloride
(VIe). Yield 68 %, mp 210–212°C, Rf 0.61. IR
1
spectrum, ν, cm–1: 3320 (О–Н). Н NMR spectrum, δ,
ppm: 0.92 t (3H, CH3, J 7.4 Hz), 1.40 br.sextet (2H,
CH2, J 7.4 Hz), 1.63 m(2Н, СН2), 3.05 br (1Н), 3.15
br [(3Н) N(CH2)2], 3.48–3.56 m ( 2H, CH2), 3.71–3.96
m [ 5Н, O(CH2)2 , СН], 3.62 s (3Н, CH3), 4.13 br (1Н,
CH), 4.79 br.d (1Н, CH, J 10.0 Hz), 5.30 br (1H,
OH), 6.40 d (2H, J 8.64 Hz), 6.76 d (2H, С6Н4, J
8.64 Hz), 6.93 (1H, J 8.1 Hz), 7.04–7.10 m (3H), 7.18
br.t (1H, J 7.6 Hz), 7.24 br (2H), 7.29 br.t (1H, J
7.7 Hz), 8.43 br.d (1H, 9Haryl., J 7.7 Hz), 12.83 br
(1H, HCl). Found, %: C 70.36; H 7.41; N 2.72; Cl
6.92. C30 H37 NO4·HCl. Calculated, %: C 70.38; Н
7.42; N 2.73; Cl 6. 94.
3-[4-(3-Methylbutoxy)phenyl]-1-(morpholin-4-
yl)-2-phenyldecan-3-ol hydrochloride (VIj). Yield
71%, mp 186–187oC, Rf 0.64. IR spectrum, ν, cm–1:
1
3350 (О–Н). Н NMR spectrum, δ, ppm: 0.84 t ( 3H,
CH3, J 6.6 Hz), 0.84 br (2Н, CH2), 0.98 d (6Н, 2СН3,
J 6.6 Hz), 1.11 br (12Н, 6СН2), 1.64 q (2Н, СН2, J
6.6 Hz), 1.81 m (2H, CH2), 1.82 (1Н, СН, J 6.6 Hz),
2.63 br. (1Н), 3.00 br [3H, N(CH2)2], 3.38 br (1Н,
CH), 3.9 t ( 2Н, OCH2, J 6.6 Hz), 3.65–4.09 br [6H, O
(CH2)2, 2СН, J 6.6 Hz], 5.14 br (1Н, ОН), 6.64 d (2H,
J 8.8 Hz), 6.84 d (2H, C6H4, J 8.8 Hz), 6.85 br (2H),
7.14–7.18 m (3H, C6H5), 11.81 br (1Н, HCI). Found,
%: C 71.86; H 9.25; N 2.69; Cl 6.83. C31H47NO3·HCl.
Calculated, %: C 71.88; Н 9.27; N 2.70; Cl 6.85.
2-[4-(3-Methylbutoxy)phenyl]-4-(morpholin-4-
yl)-3-phenylbutan-2-ol hydrochloride (VIf). Yield
67%, mp 198–200°C, Rf 0.62. IR spectrum, ν, cm–1:
1
3315(О–Н). Н NMR spectrum, δ, ppm: 0.98 d (6Н,
СН3, J 6.6 Hz), 1.65 q (2Н, СН2, J 6.6 Hz), 1.64 s (3H,
CH3), 1.76–1.92 t (1H, CH), 3.93 t (2Н, OCH2, J
6.6 Hz), 2.63m (1H), 2.97–3.16 m [3Н, N(CH2)2],
3.69–3.90 m J 8.9 Hz), 6.81–6.88 m (4H), 7.15–7.19
m (3H, 9Harom), 11.73 br (1Н, HCI). Found, %: C
69.19; H 8.29; N 2.71; Cl 8.16. C25H35NO3·HCl.
Calculated, %: C 69.20; Н 8.30; N 3.22; Cl 8.18.
IR spectra were recorded on a spectrophotometer
1
Nicolet Avatar 330 FT-IR. H NMR spectra were
registered on a spectrometer Mercury VX-300
(300.08 MHz) from solutions in a mixture DMSO-d6–
CF3COOD, internal reference TMS. Melting points of
compounds obtained were measured on a Boetius
heating block. The homogeneity of compounds was
checked by TLC on Silufol-254 plates, eluent 1-butanol–
ethanol–acetic acid–water, 8 : 2 : 1 : 3, development in
iodine vapor.
3-[4-(3-Methylbutoxy)phenyl]-1-(morpholin-4-
yl)-2-phenylheptan-3-ol hydrochloride (VIh). Yield
76%, mp 145–146°C, Rf 0.64, IR spectrum, ν, cm–1:
1
3340 (О–Н). Н NMR spectrum, δ, ppm: 0.84 m (3H,
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 50 No. 8 2014