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3-{3-Oxo-3-[4-(propan-2-yloxy)phenyl]propyl-
(1H, NH), 4.22 q (2H, OCH2, J = 7.1), 6.54–6.59 m
(2H, 2-H, 6-H), 7.44–7.50 m (2H, m-H), 7.53–7.60 m
(1H, p-H), 7.67–7.72 m (2H, 3-H, 5-H), 7.93–7.98 m
(2H, o-H). Found, %: C 72.84; H 6.13; N 4.85.
C18H19NO3. Calculated, %: C 72.71; H 6.44; N 4.71.
amino}benzoic acid (6). Yield 57%, mp 161–162°C,
Rf 0.68. IR spectrum, ν, cm–1: 3363 (NH), 1694 (COOH),
1
1670 (C=O). H NMR spectrum, δ, ppm (J, Hz): 1.34
d (6H, CH3, J = 6.1), 3.20 t (2H, CH2, J = 6.6), 3.46 t
(2H, NCH2, J = 6.6), 4.68 sept (1H, CH, J = 6.1), 5.45
br.s (1H, NH), 6,75 d.d.d (1H, 6-H, J = 7.6, 2.3, 1.4),
6.86–6.91 m (2H, 3′-H, 5′-H), 7.09–7.20 m (3H, 2-H,
4-H, 5-H), 7.87–7.92 m (2H, 2′-H, 6′-H), 12.07 br.s
(1H, COOH). Found, %: C 69.50; H 6.58; N 4.50.
C19H21NO4. Calculated, %: C 69.71; H 6.47; N 4.28.
Ethyl-4-[3-(4-chlorophenyl)-3-oxopropylamino]-
benzoate (11). Yield 98%, mp 207–208°C, Rf 0.67. IR
spectrum, ν, cm–1: 3367 (NH), 1694 (COOEt), 1680
(C=O). 1H NMR spectrum, δ, ppm (J, Hz): 1.34 t (3H,
CH3, J = 7.1), 3.28 t (2H, CH2, J = 6.6), 3.51 t (2H,
NCH2, J = 6.6), 4.22 q (2H, OCH2, J = 7.1), 6.16 br.s
(1H, NH), 6.52–6.57 m (2H, 2-H, 6-H), 7.45–7.50 m
(2H, 3′-H, 5′-H), 7.67–7.72 m (2H, 3-H, 5-H), 7.92–
7.97 m (2H, 2′-H, 6′-H). Found, %: C 65.37; H 5.50;
Cl 10.42; N 4.10. C18H18ClNO3. Calculated, %: C
65.16; H 5.47; Cl 10.68; N 4.22.
4-(3-Oxo-3-phenylpropylamino)benzoic acid (7).
Yield 59%, mp 145–147°C, Rf 0.67. IR spectrum, ν,
1
cm–1: 3350 (NH), 1680 (C=O). H NMR spectrum, δ,
ppm (J, Hz): 3.60 t (2H, CH2, J = 5.5), 3.95 t (2H,
NCH2, J = 5.5), 7.51–7.58 m (2H, C6H5), 7.67–7.75 m
(3H, C6H5), 7.94–7.99 m (2H, C6H4), 8.27–8.33 m
(2H, C6H4). Found, %: C 71.91; H 5.40; N 5.30.
C16H15NO3. Calculated, %: C 71.36; H 5.61; N 5.20.
Ethyl 4-[3-(4-methoxyphenyl)-3-oxopropylamino]-
benzoate (12). Yield 88%, mp 243–245°C, Rf 0.70. IR
spectrum, ν, cm–1: 3387 (NH), 1694 (COOEt), 1680
(C=O). 1H NMR spectrum, δ, ppm (J, Hz): 1.34 t (3H,
CH3, J = 7.1), 3.22 t (2H, CH2, J = 6.6), 3.50 t (2H,
NCH2, J = 6.6), 3.87 s (3H, OCH3), 4.22 q (2H, OCH2,
J = 7.1), 6.13 br.s (1H, NH), 6.52–6.57 m (2H, 2-H, 6-
H), 6.91–6.96 m (2H, 3′-H, 5′-H), 7.66–7.71 m (2H, 3-
H, 5-H), 7.90–7.95 m (2H, 2′-H, 6′-H). Found, %: C
69.55; H 6.26; N 4.55. C19H21NO4. Calculated, %: C
69.71; H 6.47; N 4.28.
4-[3-(4-Ethoxyphenyl)-3-oxopropylamino]benzoic
acid (8). Yield 59%, mp 145–147°C, Rf 0.72. IR spec-
trum, ν, cm–1: 3350 (NH), 1680 (C=O). 1H NMR spec-
trum, δ, ppm (J, Hz): 1.35 t (3H, CH3, J = 6.9), 3.25 t
(2H, CH2, J = 6.6), 3.44 t.d (2H, NCH2, J = 6.6, 5.5),
4.12 q (2H, OCH2, J = 6.9), 6.42 t (1H, NH, J = 5.5),
6.56–6.61 m (2H, 2-H, 6-H), 6.99–7.05 m (2H, 3′-H,
5′-H), 7.64–7.69 m (2H, 2′-H, 6′-H), 7.90–7.95 m (2H,
3-H, 5-H), 11.95 br.s (1H, COOH). Found, %: C 69.29;
H 6.30; N 4.60. C18H19NO4. Calculated, %: C 69.00; H
6.11; N 4.47.
Ethyl 4-{3-oxo-3-[4-(propan-2-yloxy)phenyl]propyl-
amino}benzoate (13). Yield 68%, mp 155–156°C, Rf
0.71. IR spectrum, ν, cm–1: 3391, 3363 (NH), 1698
1
(COOEt), 1675 (C=O). H NMR spectrum, δ, ppm
4-{3-Oxo-3-[4-(propan-2-yloxy)phenyl]propyl-
amino}benzoic acid (9). Yield 80%, mp 229–231°C,
Rf 0.67. IR spectrum, ν, cm–1: 3360 (NH), 1665 (C=O).
1H NMR spectrum, δ, ppm (J, Hz): 1.06 t (3H, CH3,
J = 7.4), 1.82 t (2H, CH3CH2), 3.21 t (2H, CH2CH2N,
J = 6.6), 3.49 t. d (2H, NHCH2, J = 6.6, 5.7), 3.99 t
(2H, OCH2, J = 6.5), 5.96 s (1H, NH), 6.04 t (1H, NH,
J = 5.7), 6.55 m (2H, 2-H, 6-H), 6.91 m (2H, 3′-H, 5′-H),
7.68 m (2H, 3-H, 5-H), 7.90 m (2H, 2′-H, 6′-H), 11.51
br.s (1H, COOH). Found, %: C 69.47; H 6.58; N 4.14.
C19H21NO4. Calculated, %: C 69.71; H 6.47; N 4.28.
(J, Hz): 1.34 t (3H, CH3CH2O, J = 7.0), 1.35 d (6H,
CH3, J = 6.0), 3.21 t (2H, CH2, J = 6.6), 3.50 t (2H,
NCH2, J = 6.6), 4.22 q (2H, OCH2, J = 7.0), 4.68 sept
(1H, OCH, J = 6.0), 6.12 br.s (1H, NH), 6.52–6.57 m
(2H, 2-H, 6-H), 6.86–6.91 m (2H, 3′-H, 5′-H), 7.66–
7.71 m (2H, 3-H, 5-H), 7.86–7.91 m (2H, 2′-H, 6′-H).
Found, %: C 70.75; H 7.26; N 4.11. C21H25NO4.
Calculated, %: C 70.96; H 7.09; N 3.94.
2-(Diethylamino)ethyl 4-(3-oxo-3-phenylpropyl-
amino)benzoate (14). Yield 67%, mp 201–204°C, Rf
0.67. IR spectrum, ν, cm–1: 3372 (NH), 1676 (C=O).
1H NMR spectrum, δ, ppm (J, Hz): 1.04 t (6H, CH3,
J = 7.1), 2.56 q (4H, NCH2CH3, J = 7.1), 2.73 t (2H,
NCH2CH2O, J = 6.3), 3.29 t [2H, C(O)CH2, J = 6.6],
3.52 t. d (2H, NHCH2, J = 6.6, 5.7), 4.19 t (2H, OCH2,
J = 6.4), 6.17 br.t (1H, NH, J = 5.7), 6.53–6.58 m (2H,
2-H, 6-H), 7.44–7.50 m (2H, m-H), 7.53–7.59 m (1H,
p-H), 7.66–7.71 m (2H, 3-H, 5-H), 7.94–7.98 m (2H,
Compounds 10–17 were synthesized in a similar
way from benzocaine or novocaine.
Ethyl 4-(3-oxo-3-phenylpropylamino)benzoate (10).
Yield 34%, mp 163–164°C, Rf 0.67. IR spectrum, ν,
1
cm–1: 3379 (NH), 1677 (C=O). H NMR spectrum, δ,
ppm (J, Hz): 1.34 t (3H, CH3, J = 7.1), 3.29 t (2H,
CH2, J = 6.6), 3.53 t (2H, NCH2, J = 6.6), 3.74 br.s
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 87 No. 2 2017