5926
Z.-W. Chen et al. / Tetrahedron 67 (2011) 5920e5927
MS (EI) m/z: 44, 58, 72, 83,100,110, 209. Anal. Calcd for C12H16FNO: C,
68.88; H, 7.71; N, 6.69. Found: C, 68.71; H, 7.75; N, 6.74.
J¼6.4 Hz, 3H), 0.82 (t, J¼6.4 Hz, 3H). 13C NMR (100 MHz, CDCl3):
d
¼172.5, 42.0, 40.0, 33.1, 31.7, 29.4, 29.1, 25.5, 22.5, 14.3, 14.0, 13.0.
MS (EI) m/z: 58, 86, 112, 156, 184, 199. Anal. Calcd for C12H25NO: C,
4.2.22. N,N-Diethyl-2-(2-fluorophenyl)acetamide (3ja). IR (KBr):
72.31; H, 12.64; N, 7.03. Found: C, 72.13; H, 12.70; N, 7.11.
2938, 2917, 1645, 1513, 1426, 1255, 1203, 1138, 824. 1H NMR
(400 MHz, CDCl3):
7.00e7.10 (m, 2H), 3.69 (s, 2H), 3.36e3.42 (m, 2H), 3.30e3.36 (m,
2H), 1.10e1.15 (m, 6H). 13C NMR (100 MHz, CDCl3):
159.4,131.0,130.9,128.5,128.4,124.1,124.1,122.8,122.6,115.2,115.0,
42.2, 40.3, 33.2,14.1,12.9. MS (EI) m/z: 44, 58, 72,100,109, 209. Anal.
Calcd for C12H16FNO: C, 68.88; H, 7.71; N, 6.69. Found: C, 68.96; H,
7.74; N, 6.63.
d
¼7.28e7.32 (m, 1H), 7.19e7.24 (m, 1H),
4.2.29. N,N-Diethyl-2-oxo-2-phenylacetamide (4aa). IR (KBr): 2977,
2933, 1681, 1640, 1446, 1228, 1144, 721. 1H NMR (400 MHz, CDCl3):
d
¼169.1, 161.8,
d
¼7.89e7.91 (m, 2H), 7.58e7.62 (m, 1H), 7.45e7.49 (m, 2H),
3.50e3.56 (m, 2H), 3.18e3.23 (m, 2H), 1.25 (t, J¼6.4 Hz, 3H), 1.12 (t,
J¼6.4 Hz, 3H). 13C NMR (100 MHz, CDCl3):
¼191.6, 166.7, 134.5,
d
133.2, 129.6, 128.9, 42.1, 38.8, 14.1, 12.8. MS (EI) m/z: 44, 51, 72, 77,
100, 105, 205. Anal. Calcd for C12H15NO2: C, 70.22; H, 7.37; N, 6.82.
Found: C, 70.04; H, 7.42; N, 6.91.
4.2.23. 2-(4-Bromophenyl)-N,N-diethylacetamide (3ka). IR (KBr):
2974, 2932, 1643, 1456, 1318, 1132, 1012, 797. 1H NMR (400 MHz,
Acknowledgements
CDCl3):
d
¼7.34 (d, J¼8.4 Hz, 2H), 7.05 (d, J¼8.4 Hz, 2H), 3.54 (s, 2H),
7.27e7.32 (m, 2H), 7.18e7.23 (m, 2H), 1.03 (t, J¼7.2 Hz, 6H). 13C NMR
The authors thank the National Natural Science Foundation of
China (Nos. 20625205, 20772034, and 20932002), National Basic
Research Program of China (973 Program) (2011CB808600), Doc-
toral Fund of Ministry of Education of China (20090172110014), and
Guangdong Natural Science Foundation (10351064101000000) for
financial support.
(100 MHz, CDCl3):
d¼169.4, 134.5, 131.5, 130.6, 120.5, 42.3, 40.2,
39.9, 14.2, 12.9. MS (EI) m/z: 44, 58, 72, 89, 100, 171, 269. Anal. Calcd
for C12H16BrNO: C, 53.35; H, 5.97; N, 5.18. Found: C, 53.17; H, 6.04;
N, 5.25.
4.2.24. 2-(3-Fluorophenyl)-1-morpholinoethanone (3ih). IR (KBr):
2976, 2934, 1644, 1589, 1453, 1264, 1137, 776, 735, 684. 1H NMR
References and notes
(400 MHz, CDCl3):
d
¼7.24e7.29 (m, 1H), 6.91e7.00 (m, 3H), 3.69 (s,
2H), 3.62 (s, 4H), 3.50 (d, J¼3.6 Hz, 2H), 3.42 (d, J¼3.6 Hz, 2H). 13C
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NMR (100 MHz, CDCl3):
d¼168.9, 164.1, 161.6, 137.2, 137.1, 130.2,
130.1, 124.3, 124.3, 115.7, 115.5, 114.0, 113.7, 66.7, 66.4, 46.4, 42.1,
40.2. MS (EI) m/z: 56, 70, 83, 109, 114, 223. Anal. Calcd for
C12H14FNO2: C, 64.56; H, 6.32; N, 6.27. Found: C, 64.34; H, 6.39;
N, 6.34.
4.2.25. 2-(3-Chlorophenyl)-1-morpholinoethanone (3lh). IR (KBr):
2964, 2920, 2856, 1644, 1573, 1432, 1230, 1115, 1073, 766, 683. 1H
NMR (400 MHz, CDCl3):
3.65 (s, 2H), 3.60 (s, 4H), 3.49 (t, J¼4.4 Hz, 2H), 3.39 (t, J¼4.4 Hz, 2H).
13C NMR (100 MHz, CDCl3):
d¼7.18e7.25 (m, 3H), 7.08 (d, J¼6.8 Hz, 1H),
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Harms, K.; Studer, A. Org. Lett. 2004, 6, 3477; (g) Shendage, D. M.; Frohlich, R.;
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d
¼168.9, 136.7, 134.4, 129.9, 128.8, 127.1,
126.9, 66.7, 66.4, 46.4, 42.1, 40.1. MS (EI) m/z: 42, 70, 89, 114, 125,
239. Anal. Calcd for C12H14ClNO2: C, 60.13; H, 5.89; N, 5.84. Found:
C, 59.91; H, 5.96; N, 5.93.
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(3mh). IR (KBr): 2967, 2922, 2858, 1648, 1427, 1314, 1160, 1109, 962,
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4. Yao, L.; Aube, J. J. Am. Chem. Soc. 2007, 129, 2766.
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d
¼7.59 (d, J¼8.0 Hz, 1H),
7.43e7.47 (m,1H), 7.29e7.32 (m, 2H), 3.80 (s, 2H), 3.60 (s, 4H), 3.53 (t,
J¼4.4 Hz, 2H), 3.38 (t, J¼4.4 Hz, 2H). 13C NMR (100 MHz, CDCl3):
d
¼168.6, 133.4, 133.4, 131.9, 131.5, 128.8, 128.5, 128.2, 127.9, 127.1,
126.1, 126.1, 126.0, 126.0, 125.7, 123.0, 120.3, 66.7, 66.4, 46.1, 42.2,
36.9. MS (EI) m/z: 56, 70, 109, 114, 159, 204, 273. Anal. Calcd for
C13H14F3NO2: C, 57.14; H, 5.16; N, 5.13. Found: C, 57.31; H, 5.10;
N, 5.21.
4.2.27. 2-(3,5-Bis(trifluoromethyl)phenyl)-1-morpholinoethanone
(3nh). IR (KBr): 2924, 2858,1649,1437,1376,1280,1173, 1129,1038,
898. 1H NMR (400 MHz, CDCl3):
d
¼7.75 (s, 1H), 7.66 (s, 2H), 3.78 (s,
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Ramon, R. S.; Bosson, J.; Díez-Gonzalez, S.; Marion, N.; Nolan, S. P. J. Org. Chem.
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3599.
CDCl3):
d¼167.8, 137.2, 132.2, 131.9, 131.5, 131.2, 129.6, 129.5, 127.3,
124.5, 121.8, 121.1, 121.0, 121.0, 121.0, 120.9, 119.1, 66.7, 66.4, 46.2,
42.3, 39.3. MS (EI) m/z: 56, 70, 86, 114, 177, 227, 341. Anal. Calcd for
C14H13F6NO2: C, 49.27; H, 3.84; N, 4.10. Found: C, 49.13; H, 3.88;
N, 4.14.
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4.2.28. N,N-Diethyloctanamide (3oa). IR (KBr): 2927, 1730, 1647,
1459, 1376, 1266, 1146, 1098, 791. 1H NMR (400 MHz, CDCl3):
d
¼3.29e3.32 (m, 2H), 3.24e3.29 (m, 2H), 2.24 (t, J¼8.0 Hz, 2H),
1.54e1.62 (m, 2H), 1.20e1.26 (m, 8H), 1.11 (t, J¼6.4 Hz, 3H), 1.05 (t,