8
34
SHAKHMAEV et al.
+
(
I , %): 193 (5) [M] , 180 (20), 178 (32), 132 (17),
CHarom), 128.23 (4C, CHarom), 128.31 (4C, CHarom),
rel
7
3
7 (33), 75 (100), 68 (49), 56 (10), 49 (9), 42 (13),
9 (29).
142.27 (2C, C ). Mass spectrum, m/z (I , %): 281
arom
rel
+
(4) [M] , 177 (6), 176 (49), 91 (37), 73 (5), 72 (100),
5 (5), 58 (9), 44 (4), 42 (4), 41 (5). Found, %:
C 85.18; H 9.53; N 4.77 C H N. Calculated, %:
6
(
2E)-N-Ethyl-3-phenyl-N-[(2E)-3-phenylprop-2-
en-1-yl]prop-2-en-1-amine (4). A solution of 0.3 g
1.55 mmol) of amine 2, 10.6 mg (0.03 mmol) of
2
0
27
C 85.35; H 9.67; N 4.98.
(
Fe(acac) , and 18 mg (0.15 mmol) of N,N,N′,N′-tetra-
This study was performed under financial support
by the Ministry of Education and Science of the
Russian Federation in the framework of the base part
of state assignment in the sphere of research activity
(project no. 4.6451.2017/8.9).
3
methylethane-1,2-diamine in 3 mL of anhydrous THF
was cooled to 0°C, and 5.6 mL of a 1 M solution of
phenylmagnesium bromide in THF was slowly added
under argon. The mixture was stirred for 2 h at room
temperature, 2 mL of degassed water was added, and
the mixture was extracted with ethyl acetate (3×5 mL).
The combined extracts were washed with brine, dried
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–
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0
2
.342 g (80%). IR spectrum, ν, cm : 3025, 2968,
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6
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3
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10H, Harom). C NMR spectrum, δ , ppm: 11.70
С
(
CH ), 47.13 (CH CH N), 55.64 (2C, CH CH=),
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3
2
2
6
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+
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rel
118 (12), 117 (100), 116 (10), 115 (44), 91 (30), 71
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(
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N-Ethyl-3-phenyl-N-(3-phenylpropyl)propan-
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9
. Cahiez, G. and Avedissian, H., Synthesis, 1998, p. 1199.
1
(
1
0. Dohle, W., Kopp, F., Cahiez, G., and Knochel, P.,
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1
9
.8 mL of a 0.1 M solution of sodium hydroxide in
5% ethanol was stirred in a hydrogen atmosphere
1
1. Seck, M., Franck, X., Hocquemiller, R., Figadère, B.,
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1 atm) until complete conversion of amine 4 (8 h,
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centrated, and the product was purified by column
chromatography on silica gel using hexane–ethyl
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1
1
1
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–
1
spectrum, ν, cm : 3026, 2939, 2860, 2800, 1496,
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1
1
454, 1079, 1031, 746, 698. H NMR spectrum, δ,
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3
15. Shakhmaev, R.N., Sunagatullina, A.Sh., and Zorin, V.V.,
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2
2
2
7
.6 Hz), 2.52 q (2H, CH CH N, J = 7.1 Hz), 2.60 t
3 2
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4H, CH CH N, J = 7.6 Hz), 7.14–7.28 m (10H,
2 2
1
3
Harom). C NMR spectrum, δ , ppm: 11.52 (CH ),
C
3
2
8.56 (2C, CH CH N), 33.71 (2C, PhCH ), 47.37
17. Shakhmaev, R.N., Sunagatullina, A.Sh., and Zorin, V.V.,
2
2
2
(
CH CH N), 52.83 (2C, CH CH N), 125.65 (2C,
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3
2
2
2
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 53 No. 6 2017