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Convenient synthesis and NMR spectral studies of variously substituted N-methylpiperidin-4-one-O-benzyloximes

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Abstract

A series of variously substituted N-methylpiperidin-4-one-O-benzyloximes were synthesized by three different methods. Among them, the direct conversion of 2,6-diarylpiperidin-4-ones into the corresponding oxime ethers (method A) was proved to be better than the other two methods in the sense of good yield, convenience, easy work-up and quick reaction time. All the synthesized compounds are characterized by IR, Mass and NMR (1H NMR, 13C NMR, 1H-1H COSY, 1H-13C COSY and HMBC) spectral studies. The conformational preference of the synthesized oxime ethers with/without alkyl and aryl substituents at C-3/C-5 and C-2/C-6 is discussed using the spectral data. The observed chemical shifts and coupling constants suggest that the synthesized oxime ethers adopt chair conformation with equatorial orientation of all the substituents, whereas 1-methyl-3-isopropyl-2,6-diphenylpiperidin-4-one-O-benzyloxime also exists in boat conformation. Based on the NMR data, the effects of oximination on ring carbons and their associated protons and alkyl substituents are discussed. In addition, the effect of NMe group on the 2,6-diarylpiperidin-4-one-O-benzyloximes was also studied.

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References

  1. Geneste P, Kamenka JM, Hugon I, Graffin P (1976) J Org Chem 22:3637

    Article  Google Scholar 

  2. Caldwell CW, Gauthier AD, Grew MN (1993) Magn Reson Chem 31:309

    Article  CAS  Google Scholar 

  3. Noller CR, Baliah V (1948) J Am Chem Soc 70:3853

    Article  CAS  Google Scholar 

  4. Balasubramanian M, Padma N (1954) Tetrahedron 19:2135

    Article  Google Scholar 

  5. Baliah V, Gopalakrishnan V, Govindarajan TS (1954) J Indian Chem Soc 31:832

    CAS  Google Scholar 

  6. Baliah V, Gopalakrishnan V (1954) J Indian Chem Soc 31:250

    CAS  Google Scholar 

  7. Baliah V, Ekambaram A (1955) J Indian Chem Soc 32:274

    CAS  Google Scholar 

  8. Radhakrishnan TR, Balasubramanian M, Baliah V (1972) Indian J Chem 11:318

    Google Scholar 

  9. Berlin KD, Ramalingam K, Satyamurthy N, Sivakumar R (1979) J Org Chem 44:471

    Article  Google Scholar 

  10. Pandiarajan K, Sekar R (1981) Indian J Chem 20B:686

    CAS  Google Scholar 

  11. Pandiarajan K, Sabapathy mohan RT, Krishnakumar R (1987) Indian J Chem 26B:624

    CAS  Google Scholar 

  12. Sivasubramanian S, Sundharavadivelu M, Arumugam N (1981) Indian J Chem 20B:878

    CAS  Google Scholar 

  13. Pandiarajan K, Sekar R, Anantharaman R, Ramalingam V, Marko D (1991) Indian J Chem 30B:490

    CAS  Google Scholar 

  14. Krishnapillay M, Fazal Mohamed MI (1997) Indian J Chem 36B:50

    CAS  Google Scholar 

  15. Pandiarajan K, Jegdish TN, Benny JCN (1997) Indian J Chem 36B:662

    CAS  Google Scholar 

  16. Lunazzi L, Macciantelli D, Tassi D, Dondoi A (1980) J Chem Soc Perkin Trans-2, 717

  17. Lunazzi L, Macciantelli D, Cerioni G (1982) J Org Chem 47:4579

    Article  CAS  Google Scholar 

  18. Rubiralta M, Macro MP, Feliz M, Giralt E (1989) Heterocycles 29:2185

    Article  CAS  Google Scholar 

  19. Ravindran T, Jeyaraman R, Murray RW, Singh MJ (1991) J Org Chem 56:4833

    Article  CAS  Google Scholar 

  20. Senthilkumar UP, Jeyaraman R, Murray RW, Singh MJ (1992) J Org Chem 57:6006

    Article  CAS  Google Scholar 

  21. Krishnakumar R, Krishnapillay M (1992) Indian J Chem 31B:438

    Google Scholar 

  22. Gdaniec M, Milewska MJ, Polonski T (1995) J Org Chem 60:7411

    Article  CAS  Google Scholar 

  23. Krishnakumar R, Krishnapillay M (1996) Indian J Chem 35B:418

    CAS  Google Scholar 

  24. Krishnapillay M, Krishnakumar R, Nagarajan A, Jeyaraman G (2000) Indian J Chem 39B:419

    CAS  Google Scholar 

  25. Aridoss G, Balasubramanian S, Parthiban P, Kabilan S (2007) Spectrochim Acta 68A:1153

    CAS  Google Scholar 

  26. Hawker GE, Herwing K, Roberts JD (1974) J Org Chem 39:2017

    Google Scholar 

  27. Pandiarajan K, Sabapathi mohan RT, Hasan MU (1986) Mag Reson Chem 24:312

    Article  CAS  Google Scholar 

  28. Parthiban P, Balasubramanian S, Aridoss G, Kabilan S (2008) Spectrochim Acta 70A:11

    CAS  Google Scholar 

  29. Pandiarajan K, Tamilselvi P, Gurumani V (1994) Indian J Chem 33B:971

    CAS  Google Scholar 

  30. Gurumani V, Pandiarajan K, Swaminathan M (1997) Bull Chem Soc Jpn 70:29

    Article  CAS  Google Scholar 

  31. Bhaskar reddy D, Somasekhar reddy A, Padmavathi V (1999) Indian J Chem 38B:141

    Google Scholar 

  32. Ziriakus W, Haller R (1972) Arch Pharm 814

  33. Manimekalai A, Jayabharathi J, Rufina L, Mahendiran R (2003) Indian J Chem 42B:2074

    CAS  Google Scholar 

  34. Rameshkumar N, Veena A, Ilavarasan R, Adiraj M, Shanmugapandiyan P, Sridhar SK (2003) Biol Pharm Bull 26:188

    Article  CAS  Google Scholar 

  35. Manimekalai A, Senthilsivakumar B, Maruthavanan T (2004) Indian J Chem 43B:1753

    CAS  Google Scholar 

  36. Manimekalai A, Jeyabharathi J, Sankardoss R (2004) Indian J Chem 43B:1018

    CAS  Google Scholar 

  37. Booth H (1966) Tetrahedron 22:615

    Article  CAS  Google Scholar 

  38. Aridoss G, Balasubramanian S, Parthiban P, Kabilan S (2007) Med Chem Res 16:188

    Article  CAS  Google Scholar 

  39. Aridoss G, Balasubramanian S, Parthiban P, Kabilan S (2007) Eur J Med Chem 42:851

    Article  CAS  Google Scholar 

  40. Parthiban P, Balasubramanian S, Aridoss G, Kabilan S (2006) Med Chem Res 14:523

    Article  CAS  Google Scholar 

  41. Ramalingan C, Park YT, Kabilan S (2006) Eur J Med Chem 41:683

    Article  CAS  Google Scholar 

  42. Baliah V, Lakshmanan M, Pandiarajan K (1978) Indian J Chem 16B:72

    CAS  Google Scholar 

  43. Ballini R, Barboni L, Fillippone P (1997) Chem Lett 475

  44. Balasubramanian M, Padma N (1963) Tetrahedron 19:2135

    Article  CAS  Google Scholar 

  45. Jones AJ, Hasan MMA (1972) J Org Chem 37:2322

    CAS  Google Scholar 

  46. Pandiarajan K, Sekar R, Anantharaman R, Ramalingam V, Marko D (1991) Indian J Chem 30B:490

    CAS  Google Scholar 

  47. Sivasubramaniam S, Sundaravadivelu M, Arumugam N (1981) Indian J Chem 20B:878

    Google Scholar 

  48. Arumugam N, Sundaravadivelu M, Sivasubramaniam S, Wilson DA (1987) Magn Reson Chem 25:869

    Article  CAS  Google Scholar 

  49. Ravindran T, Jeyaraman R (1992) Indian J Chem 31B:677

    CAS  Google Scholar 

  50. Hawkes GE, Herwig K, Roberts JD (1974) J Org Chem 39:1017

    Article  CAS  Google Scholar 

  51. Hasan MU, Arab M, Pandiarajan K, Sekar R, Marko D (1985) Magn Reson Chem 23:293

    Google Scholar 

  52. Lambert JB, Netzel DA, Sun HN, Lilianstorm KK (1976) J Am Chem Soc 98:3778

    Article  CAS  Google Scholar 

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Acknowledgment

We are grateful to NMR Research Center, IISc, Bangalore, for providing all the NMR facilities.

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Author notes

  1. Paramasivam Parthiban

    Present address: Department of Chemistry, Indian Institute of Technology Madras, Chennai, 600 036, India

Authors and Affiliations

  1. Department of Chemistry, Annamalai University, Annamalainagar, 608 002, India

    Paramasivam Parthiban, Mannangatty Rani & Senthamaraikannan Kabilan

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  1. Paramasivam Parthiban
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  2. Mannangatty Rani
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  3. Senthamaraikannan Kabilan
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Correspondence to Senthamaraikannan Kabilan.

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Parthiban, P., Rani, M. & Kabilan, S. Convenient synthesis and NMR spectral studies of variously substituted N-methylpiperidin-4-one-O-benzyloximes. Monatsh Chem 140, 287–301 (2009). https://doi.org/10.1007/s00706-008-0021-6

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