MESROPYAN et al.
1298
(0.01 mol) of oxirane I in 1 ml of ethanol was maintained
at room temperature for 48 h, evaporated, and the residue
was subjected to vacuum distillation. Yield 2.3 g (87%)
bp 175°C (1.5 mm Hg), nD18.5 1.5485, Rf 0.46 (CHCl3–
EtOH–C6H6, 1.0:0.4:0.4). IR spectrum, ν, cm–1: 3413
(OH), 3095, 3055, 3045, 3035 (=CH, Ph), 2963, 2934,
2873, 2855, 2801 (CH, CH2, CH3), 1598 (C=C, Ph), 1105
I in 1 ml of ethanol was heated for 1 h at 150°C and kept
for 18 h at room temperature. Afterwards the reaction
mixture was extracted with hot nonane, from the cold
nonane solution a viscous substance was separated, dis-
solved in 20 ml of ethyl ether, on removing the ether the
residue crystallized. Yield 11.8 g (96%), mp 73–76°C,
Rf 0.54 (nonane–CHCl3–Me2CO, 0.2:1.0:0.2). IR spec-
trum, ν, cm–1: 3400–3320 (OH), 3200 (NH), 3095, 3065,
3045, 3030 (C–H, Ph), 2990–2840, 2720, 2670 (CH,
CH2, CH3), 1773, 1758, 1745, 1703, 1699, 1690, 1685,
1650 (C=O), 1599 (C=C, Ph), 1105 (C–O), 1250 (C–N).
1H NMR spectrum, δ, ppm: 0.95–1.19 m (3H, CH2CH3),
1.20–1.38 m (6H, CH3), 3.10–3.83 m (6H, CH2N), 4.22 m
(1H, CHOH), 3.98, 4.46, 4.60, 4.75 br.d (1H, CHOH),
6.57 t.t (1Hp, J 7.2, 1.1 Hz), 6.66 m (2Ho), 7.09 m (2Hm),
7.72, 7.90, 8.00, 8.08 s (1H, NH). Found, %: C 63.21;
H 7.32; N 13.46. C16H23N3O3. Calculated, %: C 62.93;
H 7.59; N 13.76.
1
(C–O), 1250 (C–N). H NMR spectrum, δ, ppm: 1.15 t
(3H, CH2CH3, J 7.0 Hz), 1.65 m (6H, CH2 in the ring),
2.45 q (2H, CH2CH3, J 7.0 Hz), 2.67 m (4H, CH2 in the
ring), 3.12 d.d (1H, CH2N, J 15.7, 5.0 Hz), 3.39–3.58 m
(3H, CH2N), 3.75 m (1H, CHOH), 4.00 br.s (1H, OH),
6.57 t.t (1Hp, J 7.2, 1.1 Hz), 6.66 m (2Ho), 7.11 m (2Hm).
Found, %: C 73.01; H 9.66; N 10.92. C16H26N2O. Calcu-
lated, %: C 73.24; H 9.99; N 10.68.
3-Morpholino-1-(N-ethylanilino)propan-2-ol
(XIII) was synthesized similarly. Yield 2.25 g (85%) bp
170°C (0.5 mm Hg), nD17.5 1.5526, Rf 0.51 (CHCl3–EtOH–
C6H6, 1.0:0.2:0.4). IR spectrum, ν, cm–1: 3432 (OH),
3093, 3055, 3045, 3035 (=CH, Ph), 2963, 2945, 2893,
2872, 2865, 2807, 2688 (CH3, CH2, CH), 1598 (C=C,
Ph), 1250 (C–N), 1105 (C–O). 1H NMR spectrum, δ,
ppm: 1.12 t (3H, CH2CH3, J 7.0 Hz), 2.23–2.46 m (6H,
CH2N), 3.24–3.41 m (4H, CH2NPh), 3.58 m (4H, CH2O),
3.98 m (1H, CHOH), 4.80 br.s (1H, OH), 6.57 t.t (1Hp,
J 7.2, 1.1 Hz), 6.66 m (2Ho), 7.11 m (2Hm). Found, %:
C 68.43; H 8.86; N 10.96. C15H24N2O2. Calculated, %:
C 68.15; H 9.15; N 10.60.
3-(2-Hydroxyethylamino)-1-(N-ethylanilino)
propan-2-ol (XVI). A mixture of 4.6 g (75 mmol) of
monoethanolamine and 2.65 g (15 mmol) of oxirane I in
1 ml of ethanol was kept at room temperature for 56 h.
Excess monoethanolamine and ethanol were removed,
the residue was subjected to vacuum distillation. Yield
2.6 g (72%) bp 206–207°C (1.5 mm Hg), nD20 1.5646,
Rf 0.19 (CHCl3–EtOH–C6H6, 0.4:1.2:0.4). IR spectrum,
ν, cm–1: 3400–3250 (OH), 3095, 3065, 3045, 3030 (C–H,
Ph), 2980–2800 (CH3, CH2, CH), 2599 (C=C, Ph), 1105
1
(C–O), 1250 (C–N). H NMR spectrum, δ, ppm: 1.15 t
3-(4-Methylpiperazin-1-yl)-1-(N-ethylanilino)
propan-2-ol (XIV). A mixture of 4.5 g (45 mmol) of
N-methylpiperazine and 2.65 g (15 mmol) of oxirane I
in 1 ml of ethanol was heated for 30 min at 70°C. After
keeping the mixture at room temperature for 18 h it was
evaporated, the residue was dissolved in 50 ml of ethyl
ether, filtered, on removing the ether the residue crystal-
lized. Yield 3.1 g (74%) mp 83°C, Rf 0.15 (EtOH–MeCN,
1.2:0.4). IR spectrum, ν, cm–1: 3147 (OH), 3093, 3063,
3035, 3020 (C–H, Ph), 2970–2690 (CH3, CH2, CH),
(3H, CH2CH3, J 7.0 Hz), 2.50–3.50 m (10H, CH2N, NH,
OH), 3.54 t (2H, CH2OH), 3.81 m (1H, CHOH), 4.43 br.s
(1H, OH), 6.57 t.t (1Hp, J 7.2, 1.1 Hz), 6.66 m (2HO),
7.09 m (2Hm). Found, %: C 65.83; H 9.59; N 12.01.
C13H22N2O2. Calculated, %: C 65.52; H 9.30; N 11.75.
3-(3-Hydroxypropylamino)-1-(N-ethylanilino)
propan-2-ol (XVII) was synthesized similarly from
a mixture of 3.75 g (0.05 mol) of 3-aminopropan-1-ol and
1.77 g (0.01 mol) of oxirane I in 5 ml of ethanol. Yield
2.3 g (91%) bp 191–193°C (0.5 mm Hg), nD20 1.5511,
Rf 0.14 (EtOH–MeCN, 1.2:0.4). IR spectrum, ν, cm–1:
3400–3250 (OH), 3095, 3065, 3045, 3030 (C–H, Ph),
2980–2800 (CH3, CH2, CH), 2599 (C=C, Ph), 1105
1
1599 (C=C, Ph), 1250 (C–N), 1105 (C–O). H NMR
spectrum, δ, ppm: 1.12 t (3H, CH2CH3, J 7.0 Hz), 2.15 s
(3H, NCH3), 2.20–2.50 m (10H, CH2N), 3.24–3.41 m
(4H, CH2NPh), 3.93 m (1H, CHOH), 4.56 br.s (1H, OH),
6.57 t.t (1Hp, J 7.2, 1.1 Hz), 6.66 m (2HO), 7.12 m (2Hm).
Found, %: C 69.01; H 10.09; N 15.46. C16H27N3O. Cal-
culated, %: C 69.28; H 9.81; N 15.15.
1
(C–O), 1250 (C–N). H NMR spectrum, δ, ppm: 1.15 t
(3H, CH2CH3, J 7.0 Hz), 1.62 m (2H, CH2CH2OH), 2.50–
3.50 m (10H, CH2N, NH, OH), 3.54 m (2H, CH2OH),
3.81 m (1H, CHOH), 4.43 br.s (1H, OH), 6.57 t.t (1Hp,
J 7.2, 1.1 Hz), 6.66 m (2Ho), 7.09 m (2Hm). 13C NMR
spectrum, δ, ppm: 11.1, 32.1, 44.7, 47.3, 53.3, 54.2, 60.1,
67.3, 111.3, 114.6, 120.4, 147.6. Found, %: C 66.36;
1-(5,5-Dimethylhydantoin-3-yl)-3-(N-ethyl-anilino)
propan-2-ol (XV). A mixture of 5.15 g (0.04 mol) of
5,5-dimethylhydantoine and 7.1 g (0.04 mol) of oxirane
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 46 No. 9 2010