Notes

A Practical Synthesis of 3-{[4-(2,6-Dichlorophenyl)piperidin-1-yl]- methyl}-2-(thiophen-2-yl)-1H-indole as a New Ligand for Opioid Receptor Like 1 Receptor

  • Cheng Yinan ,
  • Xie Guiying ,
  • Sun Shujun ,
  • You Xiufeng
Expand
  • Plant Protection College, Henan Agricultural University, Zhengzhou 450002

Received date: 2012-10-19

  Revised date: 2012-12-05

  Online published: 2012-12-20

Abstract

3-{[4-(2,6-Dichlorophenyl)piperidin-1-yl]methyl}-2-(thiophen-2-yl)-1H-indole (1) as a ligand for opioid receptor like 1 receptor was prepared via four steps from commercially available phenylhydrazine (2), 1-(thiophen-2-yl)- ethanone (3), 2,6-dichloro- phenyl-boronic acid (5) and 4-bromopyridine (6). This convenient approach was green and had potential application for the scale production because of recoverable reaction medium, simple isolating process of intermedi-ates, little waste and highly total yield of 65%.

Cite this article

Cheng Yinan , Xie Guiying , Sun Shujun , You Xiufeng . A Practical Synthesis of 3-{[4-(2,6-Dichlorophenyl)piperidin-1-yl]- methyl}-2-(thiophen-2-yl)-1H-indole as a New Ligand for Opioid Receptor Like 1 Receptor[J]. Chinese Journal of Organic Chemistry, 2013 , 33(03) : 630 -633 . DOI: 10.6023/cjoc201210038

References

[1] Zaveri, N. Life Sci. 2003, 73, 663.

[2] Consonni, A.; Del Sordo, S.; Farina, C.; Gagliardi, S.; Ronzoni, S.; Vallese, S. WO 2005005411, 2005 [Chem. Abstr. 2005, 142, 134473].

[3] (a) Ogata, K.; Nagaya, T.; Fukuzawa, S. J. Organomet. Chem.2010, 695, 1675.
(b) Sakai, H.; Tsutsumi, K.; Morimoto, T.; Kakiuchi, K. Adv. Synth. Catal. 2008, 350, 2498.
(c) Carpita, A.; Ribecai, A.; Stabile, P. Tetrahedron 2010, 66, 7169.
(d) Mao, H.; Wan, J. P.; Pan, Y. J.; Sun, C. R. Tetrahedron Lett. 2010, 51, 1844.
(e) Pei, T.; Tellers, D. M.; Streckfuss, E. C.; Chen, C. Y.; Davies, I. W. Tetrahedron 2009, 65, 3285.
(f) Jiang, J. Z.; Wang, Y. Chin. J. Org. Chem. 2006, 26, 1025 (in Chinese).
(蒋金芝, 王艳, 有机化学, 2006, 26, 1025.)

[4] Lemster, T.; Pindur, U.; Lenglet, G.; Depauw, S.; Dassi, C. Eur. J. Med. Chem. 2009, 44, 3235.

[5] Nishiguchi, T.; Imai, H.; Hirose, Y.; Fukuzumi, K. J. Catal. 1976, 41, 249.

[6] (a) Dillon, J. L.; Spector, R. H.; Madding, G. D.; Wire, M. E. J. Heterocycl. Chem. 1993, 30, 707.
(b) Chenevert, R.; Dickman, M. Tetrahedron: Asymmetry 1992, 3, 1021.

[7] Amour, D. R.; Chung, K. M. L.; Congreve, M.; Evans, B.; Guntrip, S.; Hubbard, T.; Kay, C.; Middlemss, D.; Mordaunt, J. E.; Pegg, N. A.; Vinader, M. V.; Ward, P.; Watson, S. P. Bioorg. Med. Chem. Lett. 1996, 6, 1015.

[8] (a) Shanklin, J. R.; Johnson, C. P.; Proakis, A. G.; Barrett, R. J. J. Med. Chem. 1991, 34, 3011.
(b) Gueremy, C.; Audiau, F.; Champseix, A. J. Med. Chem. 1980, 23, 1306.
(c) Andersen, K.; Perregaard, J.; Amt, J.; Nielsen, J. B. J. Med. Chem. 1992, 35, 4823.
(d) Renaud, J.; Bischoff, S. F.; Buhl, T.; Floersheim, P.; Fournier, B.; Geiser, M.; Halleux, C.; Kallen, J.; Keller, H.; Ramage, P. J. Med. Chem. 2005, 48, 364.

[9] Chen, J. L.; Xie, Z. F.; Xing, Y. Chin. J. Org. Chem. 2011, 31, 1714 (in Chinese).
(陈君丽, 解正峰, 邢烨, 有机化学, 2011, 31, 1714.)

[10] Dai, H. G.; Li, J. T.; Li, T. S. Synth. Commun. 2006, 36, 1829.
[11] Claudio, T.; Carmela, F.; Michela, P.; Ilaria, L.; Remo, G.; Girolamo, C.; Anna, R.; Valeria, C.; David, G. L.; John, M.; Domenico, R.; Severo, S. Bioorg. Med. Chem. 2009, 17, 5080.
Outlines

/