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F. NEMATI ET AL.
General Procedure for the Synthesis of b-Aminocarbonyl
Compounds Using Acetophenone or 1,3-Diphenylpropan-2-one
A mixture of arylaldehyde (2 mmol), aniline (2 mmol), acetophenone or
1,3-diphenylpropan-2-one (2 mmol), and CSA (0.5 g) was stirred in EtOH (5 mL)
at room temperature for 10–16 h. The reaction was monitored by TLC. The products
were precipitated from the reaction mixtures, filtered off, dissolved in hot EtOH, and
left to crystallize at room temperature. The resulting crystallized product was col-
lected by filtration and washed with EtOH (95%). The b-aminocarbonyl compounds
from 1,3-diphenylpropan-2-one were separated and purified by dry flash chromato-
graphy.
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All products were characterized by IR, H NMR, and 13C NMR and were
identified by comparison of the spectral data and melting points with those reported
in literature.
Spectral (IR, 1H NMR, and 13C NMR) and analytical data of new compounds
are given.
Selected Data
2-[(Phenylamino)(4-nitrophenyl)methyl]cyclohexanone (Table 1, Entry 8).
1
mp 123–125 ꢀC, IR (KBr): v max=cmꢁ1: 3405, 1700, 1575, 1550, 1350; H NMR
(300 MHz, CDCl3, Me4Si): d 8.16 (d, J ¼ 8.77 Hz, 2H), 7.59 (d, J ¼ 8.68 Hz, 2H),
7.13–7.08 (m, 2H), 6.70 (t, J ¼ 7.32 Hz, 1H), 6.53 (d, J ¼ 7.92 Hz, 2H), 4.72 (d,
J ¼ 5.35 Hz, anti, 1H), 2.92–2.87 (m, 1H), 2.45–2.30 (m, 2H), 2.06–1.91 (m, 3H),
1.84–1.74 (m, 3H); 13C NMR (75 MHz, CDCl3): d 24.5, 25.0, 27.0, 27.8, 29.1,
32.0, 42.4, 56.9, 58.1, 113.8, 114.1, 118.5, 123.7, 128.3, 128.6, 129.2, 129.3, 146.3,
147.1, 149.5, 211.9. Anal. calc. for C19H20N2O3: C, 70.37; H, 6.17; N, 8.64%; Found:
C, 70.25; H, 6.01; N, 8.54%.
1,3,4-Triphenyl-4-(phenylamino)butan-2-one (Table 2, Entry 10). mp
168–170 ꢀC; IR (KBr): v max=cmꢁ1: 3405, 1710, 1601, 1320, 667; 1H NMR
(300 MHz, CDCl3, Me4Si): d 7.42–7.39 (m, 2H), 7.34–7.25 (m, 8H), 7.19–7.13 m,
3H), 6.99–6.93 (m, 2H), 6.71 (dd, J ¼ 7.19, J ¼ 1.77 Hz, 2H), 6.58 (t, J ¼ 7.3 Hz,
1H), 6.34 (dd, J ¼ 8.13, J ¼ 1 Hz, 2H), 4.98 (d, anti, J ¼ 10.15 Hz, 1H), 4.14 (d,
J ¼ 10.15 Hz, 1H), 3.31 (dd, J ¼ 20, J ¼ 16 Hz, 2H); 13C NMR (75 MHz, CDCl3): d
50.7, 59.8, 64.7, 113.9, 117.8, 126.8, 127.4, 127.6, 128.3, 128.5, 128.6, 128.8, 129.1,
129.2, 129.5, 133.0, 134.7, 142.0, 147.2, 205.4; Anal. calc. for C28H25NO; C, 85.93;
H, 6.39; N, 3.58%; Found: 85.83; H, 6.28; N, 3.45%.
4-(4-Fluorophenyl)-1,3-diphenyl-4-(phenylamino)butan-2-one (Table 2,
Entry 11). mp 148–150 ꢀC; IR (KBr): v max=cmꢁ1 3428, 1700, 1600, 1508, 750,
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700; H NMR (300 MHz, CDCl3, Me4Si): d 7.38–7.30 (m, 7H), 7.2–7.15 (m, 3H),
7.0–6.9 (m, 4H), 6.72–6.7 (m, 2H), 6.62–6.57 (m, 1H), 6.30 (dd, J ¼ 8.5, J ¼ 1 Hz,
2H), 4.97 (d, anti, J ¼ 10.17 Hz, 0.88H), 4.87 (d, syn, J ¼ 4.73 Hz, 0.12H), 4.15 (d,
syn, J ¼ 7.59 Hz, 0.12H), 4.10 (d, anti, J ¼ 10.17 Hz, 0.88H), 3.74 (s, 1H), 3.37 (dd,
J ¼ 16.8, J ¼ 15.66 Hz, 2H); 13C NMR (75 MHz, CDCl3): d 50.5, 58.8, 64.6, 113.6,
113.9, 115.2, 115.5, 118.0, 126.9, 128.4, 128.6, 128.8, 129.0, 129.1, 129.2, 129.3,