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of hydrogen ceased (5 h). After the Pd–C catalyst was filtered off,
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a white crystal by filtration. Usually, it was pure enough for any
analytical purposes. It had mp 164 ꢀC (decomposed); IR:
n 3439,
´
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;
d
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2.99 (d, J¼7.89 Hz, 2H), 1.63–1.57 (m, 2H), 1.34–1.27 (m, 2H), 0.85 (t,
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d 130.9,129.8,129.7,129.3, 50.9, 46.9, 27.5,
19.2, 12.8; MS m/z (%): 163 (MꢁHCl, 1.8), 91 (100). Anal. Calcd for
C11H18ClN (199.72): C, 66.15; H, 9.08; N, 7.01. Found: C, 65.82; H,
8.96; N, 6.92.
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The similar procedure was used to convert the substrates 1b–j
efficiently to the corresponding products 5k–x$nHCl.
Acknowledgements
This work was supported by the Cultivation Fund of the Key
Scientific and Technical Innovation Project, Ministry of Education of
China (706003) and the National Natural Science Foundation of
China (30600779, 20672066).
Supplementary data
Experiments, characterization, 1H, and 13C NMR spectra for all
products 5a–x$nHCl are give in the Supplementary data. Supple-
mentary data associated with this article can be found in the online
7. Imao, D.; Fujihara, S.; Yamamoto, T.; Ohta, T.; Ito, Y. Tetrahedron 2005, 61, 6988–
6992.
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9. Cheng, C.; Wang, X.; Xing, L.; Liu, B.; Zhu, R.; Hu, Y. Adv. Synth. Catal. 2007, 349,
1775–1780.
10. (a) It is well known that Pd–C catalyzed hydrogenation is enhanced by a cata-
lytic amount of HCl, but retarded with an excess amount of HCl due to the
unproductive occupation of Pd–C catalytic sites by HCl molecules. (b) Nishi-
mura, S. Handbook of Heterogeneous Catalytic Hydrogenation for Organic Syn-
thesis; John Wiley & Sons: New York, NY, 2001; Charter 2, pp 53–59.
11. Reviews for hydrodechlorination of chloroalkanes: (a) Alonso, F.; Beletskaya, I.
P.; Yus, M. Chem. Rev. 2002, 102, 4009–4092; (b) Nishimura, S. Handbook of
Heterogeneous Catalytic Hydrogenation for Organic Synthesis; John Wiley & Sons:
New York, NY, 2001; Chart 13, pp 623–639; (c) Rylander, P. N. Hydrogenation
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References and notes
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