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D. Shanmugapriya et al.
LETTER
J. M.; Le Rouzic, A. Bull. Chem. Soc. Fr. 1975, 196.
(c) Morvan, J. M.; Kerfanto, M.; Brault, A. Bull. Chem. Soc.
Fr. 1975, 1679.
d = 1.29 (m, 3 H), 1.31 (m, 3 H), 3.2 (m, 2 H), 3.59 (m, 2 H),
7.50 (m, 2 H), 7.63 (m, 1 H), 7.93 (m, 2 H). 13C NMR (50
MHz, CDCl3): d = 12.8, 14.0, 38.8, 42.1, 128.8, 129.5,
130.0, 133.0, 133.2, 134, 166.6, 191.4. MS: m/z (%) = 206.1
[M + 1], 178.1, 130. Anal.Calcd for C12H15NO2 (205.1): C,
70.22; H, 7.37; N, 6.82. Found: C, 70.19; H, 7.31; N, 6.80.
N-Benzyl-N-methyl-2-oxo-2-phenylacetamide (2f)
IR (KBr): 723, 881, 1003, 1210, 1449, 1643, 1680, 2926,
3030, 3063 cm–1. 1H NMR (200 MHz, CDCl3): d = 2.84–
2.99 (d, 3 H), 4.39 (s, 1 H), 4.74 (s, 1 H), 7.20–7.61 (m, 8 H),
8.02–8.11 (m, 2 H), 13C NMR (50 MHz, CDCl3): d = 34.4,
49.8, 128.2, 128.7, 128.8, 128.9, 129.5, 130, 133, 133.2,
133.5, 134.6, 134.8, 135.7, 167, 191.3 MS: m/z (%) = 254.1
[M + 1], 211, 198. Anal. Calcd for C15H15NO2 (253.1): C,
75.87; H, 5.97; N, 5.53. Found: C, 75.79; H, 5.96; N, 5.50.
1-(3-Bromo-4-methoxy-phenyl)-2-piperidin-1-yl-ethane-
1,2-dione (2g)
Yield 56%. IR (KBr): 1202, 1278, 1405, 1589, 1637, 1671,
2927 cm–1. 1H NMR (200 MHz, CDCl3): d = 1.28 (m, 4 H),
1.69 (m, 2 H), 3.30 (m, 2 H), 3.70 (m, 2 H), 3.98 (s, 3 H),
6.95 (d, 1 H, J = 8.6 Hz), 7.98 (dd, 1 H, J = 2.2, 8.6 Hz), 8.15
(d, 1 H, J = 2.2 Hz). 13C NMR (50 MHz, CDCl3): d = 24.2,
25.3, 26.1, 42.1, 47.0, 56.5, 111.4, 112.4, 127.3, 131.0,
134.5, 160.7, 164.9, 189.3. MS: m/z (%) = 326.10 [M + 1],
300.0, 212.8, 148.7, 112.1. Anal. Calcd for C15H20BrNO3
(326.19): C, 51.55; H, 4.94; N, 4.29. Found: C, 51.53; H,
4.28; N, 4.83.
(25) Representative Procedure for the Synthesis of 1-Phenyl-
2-morpholin-1-yl-ethane-1,2-dione
To a solution of 2,2-dibromo-1-phenylethanone (1a, 1 g,
0.0035 mol, 1 equiv) in THF (10 mL) was added morpholine
(0.99 g, 0.014 mol, 4 equiv) dropwise over a period of 30
min at 20–30 °C. The temperature of the reaction mixture
was slowly raised to 40–50 °C under an oxygen atmosphere
and maintained for 18–26 h (monitored by TLC). After the
completion of the reaction, THF was distilled off up to 80%
of its volume. The reaction mass was then diluted with
CH2Cl2 (25 mL), washed with dil. HCl (10 mL, 4×),
followed by brine. The organic layer was then dried over
Na2SO4, and the product 2a was obtained after column
chromatographic purification in 54% of yield as off-white
solid; yield 57%.
IR (KBr): 1428, 1517, 1578, 1604, 1683, 1677, 2843 cm–1.
1H NMR (200 MHz, CDCl3): d = 3.40 (m, 2 H), 3.70 (m,
2 H), 3.80 (m, 4 H), 7.50 (m, 2 H), 7.70 (m, 1 H), 7.95 (m,
2 H). 13C NMR (50 MHz, CDCl3): d = 41.6, 46.2, 66.6, 66.7,
129.0, 129.6, 133.0, 134.8, 165.4, 191.1. MS: m/z (%) =
220.2 [M + 1], 192,159, 105. Anal. Calcd for C12H13NO3
(219.9): C, 65.74; H, 5.98; N, 6.39. Found: C, 65.71; H, 5.95;
N, 6.32.
1-Phenyl-2-piperidin-1-yl-ethane-1,2-dione (2b)
Yield 52%. IR: (KBr): 1447, 1579, 1638, 1671, 2938 cm–1.
1H NMR (200 MHz, CDCl3): d = 1.60 (m, 2 H), 1.71 (m,
4 H), 3.30 (m, 2 H), 3.71 (m, 2 H), 7.50 (m, 2 H), 7.64 (m,
1 H), 7.95 (m, 2 H). 13C NMR (50 MHz, CDCl3): d = 24.3,
25.4, 26.1, 42.1, 47.0, 128.9, 129.5, 133.2, 134.6, 165.4,
191.9. MS: m/z (%) = 218.1 [M + 1], 190.2, 149.0, 126.0.
Anal. Calcd for C13H15NO2 (203.4): C, 71.81; H, 6.96; N,
6.45. Found: C, 71.79; H, 6.91; N, 6.41.
1-Phenyl-2-pyrolidin-1-yl-ethane-1,2-dione (2c)
Yield 54%. IR (KBr): 1446, 1597, 1638, 1677, 2882, 2977
cm–1. 1H NMR (200 MHz, CDCl3): d = 1.95 (m, 4 H), 3.38
(m, 2 H), 3.65 (m, 2 H), 7.49 (m, 2 H), 7.63 (m, 1 H), 7.95
(m, 2 H). 13C NMR (50 MHz, CDCl3): d = 23.8, 25.7, 45.0,
46.5, 128.7, 129.6, 132.7, 134.4, 165.8, 191.4. MS: m/z (%)
= 204.1 [M + 1], 176.3, 105. Anal. Calcd for C12H13NO2
(203.4): C, 70.92; H, 6.45; N, 6.89. Found: C, 70.89; H, 6.45;
N, 6.89.
1-(3-Bromo-4-methoxy-phenyl)-2-pyrolidin-1-yl-ethane-
1,2-dione (2h)
Yield 57%. IR (KBr): 1264, 1499, 1589, 1629, 1642, 1665,
2980 cm–1. 1H NMR (200 MHz, CDCl3): d = 1.95 (m, 4 H),
3.40 (m, 2 H), 3.70 (m, 2 H), 3.98 (s, 3 H), 6.95 (d, 1 H,
J = 8.8 Hz), 7.98 (dd, 1 H, J = 2.2, 8.8 Hz), 8.2 (d, 1 H,
J = 2.2 Hz). 13C NMR (50 MHz, CDCl3): d = 23.9, 25.8,
45.2, 46.7, 56.5, 111.3, 112.3, 127.0, 131.4, 135.0, 160.7,
164.3, 188.9. MS: m/z (%) = 313.90 [M + 1], 312.0 [M+],
212.9, 134.8. Anal. Calcd for C13H14BrNO3 (312.36): C,
50.02; H, 4.52; N, 4.49. Found: C, 50.0; H, 4.51; N, 4.43.
1-Naphthalen-1-yl-2-morpholin-1-yl-ethane-1,2-dione
(2l)
IR (KBr):1115.7, 1226, 1252, 1273, 1628, 1669, 2923 cm–1.
1H NMR (200 MHz, CDCl3): d = 3.43 (m, 2 H), 3.65 (m,
2 H), 3.83 (m, 4 H), 7.60 (m, 3 H), 8.01 (m, 3 H), 9.20 (d,
2 H, J = 8.6 Hz). 13C NMR (50 MHz, CDCl3): d = 41.5, 46.2,
66.4, 124.3, 125.5, 126.9, 128.2, 128.6, 129.3, 130.7, 133.9,
134.3, 136.0, 165.9, 193.4 MS: m/z (%) = 270.1 [M + 1],
249, 177.4, 155.2. Anal. Calcd for C16H15NO3 (269.11): C,
71.36; H, 5.61; N, 5.20. Found: C, 71.30; H, 5.93; N, 5.52.
(26) (a) Tao, Z.; Zhen-Chu, C. J. Chem. Res., Synop. 2001, 3,
116. (b) Chen, J.; Cunico, R. F. J. Org. Chem. 2004, 65,
5509. (c) Kiyofumi, I.; Mika, K.; Takashi, Y.; Yukari, A.;
Kou, H.; Takao, S. Tetrahedron 2007, 63, 2695.
1-phenyl-2-dimethylamino-ethane-1,2-dione (2d)
Yield 48%. 1H NMR (200 MHz, CDCl3): d = 2.95 (s, 3 H),
3.11 (s, 3 H), 7.50 (m, 2 H), 7.63 (m, 1 H), 7.92 (m, 2 H). 13
C
NMR (50 MHz, CDCl3): d = 33.8, 36.9, 128.9, 129.5, 132.9,
134.6, 166.9, 191.7. MS: m/z (%) = 178.2 [M + 1], 150.2,
105.0. Anal. Calcd for C12H13NO3 (177.2): C, 67.78; H,
6.26; N, 7.90. Found: C, 67.70; H, 6.24; N, 7.89.
1-phenyl-2-diethylamino-ethane-1,2-dione (2e)
IR (KBr): 720, 855, 1146, 1233, 1383, 1448, 1642, 1681,
(27) Hasler, D. W.; Jensen, L. T.; Zerbe, O.; Winge, D. R.; Vasak,
M. Biochemistry 2000, 39, 1456.
1720, 2934, 2977 cm–1. 1H NMR (200 MHz, CDCl3):
Synlett 2008, No. 19, 2945–2950 © Thieme Stuttgart · New York