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reaction was stirred for 48 h at reflux temperature. A solution of HCl
(2 N) was added to neutralize the media. The mixture was extracted
with CH2Cl2. The organic solvent was separated and removed and
compound 12d was obtained pure after purification by chroma-
tography column eluted with n-hexane/ethyl acetate/methanol
gradient.
1H NMR (200 MHz, CDCl3):
d ppm 7.39–7.16 (m, 5H), 5.02 (dd,
J¼8.6 and 4.2 Hz, 1H), 3.21–2.73 (m, 2H), 2.89–2.71 (m, 1H), 2.46–
2.32 (m, 1H), 2.30–1.98 (m, 3H), 1.75–1.59 (m, 4H). 13C NMR
(50 MHz, CDCl3):
d ppm 143.9, 128.6, 127.7, 125.4, 71.2, 56.9, 52.9,
39.9, 26.6, 22.8, 20.4. Mp¼91.4–92.9; literature 92.0–93.0. Yield:
60% Anal. Calcd for C13H19NO: C, 76.06; H, 9.33; N, 6.82. Found: C,
76.11; H, 9.39; N, 6.88.
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Acknowledgements
38. Neto, B. A. D.; Lopes, A. S.; Wust, M.; Costa, V. E. U.; Ebeling, G.; Dupont, J.
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CAPES, CNPq for partial financial support. The authors are in
debt to Professors J. Dupont and V.E.U. Costa for helpful sugges-
tions. We also thank Roxzana Sudo (USA) for a critical reading of the
manuscript.
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Supplementary data
Supplementary data including Tables and NMR spectra is
available for the current article. Supplementary data associated
with this article can be found in the online version, at doi:10.1016/
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