Copyright (c) 2020 AJC
This work is licensed under a Creative Commons Attribution 4.0 International License.
Synthesis and Characterization of Piperidin-4-one Derivatives Using Green Solvent
Corresponding Author(s) : D. Ilangeswaran
Asian Journal of Chemistry,
Vol. 32 No. 4 (2020): Vol 32 Issue 4, 2020
Abstract
A deep eutectic solvent of glucose-urea was found to be an inexpensive and effective reaction medium in the synthesis of piperidin-4-one derivatives. In this work, 3-methyl-2,6-diphenyl piperidin-4-one (4a), 3,5-dimethyl-2,6-diphenylpiperidin-4-one (4b), 2,6-diphenylpiperidin-4-one (4c), piperidin-4-one (4d), 3,5-dimethylpiperidin-4-one (4e), 3-methyl-2,6-di(2-hydroxyphenyl)piperidin-4-one (4f), 3,5-dimethyl 2,6-di(2-hydroxyphenyl)piperidin-4one (4g) were synthesized using a deep eutectic solvent (DES) of glucose and urea with the percentage composition of 60:40. The yields of these products were 82, 78, 75, 68, 72, 70 and 70 %, respectively. The products obtained were characterized by FT-IR and 1H NMR spectroscopic techniques. A synthesis of piperidin-4-one derivatives by using this green solvent was considered to be new environmentally safe synthetic method.
Keywords
Download Citation
Endnote/Zotero/Mendeley (RIS)BibTeX
- T. Welton, Proc. Math Phys. Eng. Sci., 471, 20150502 (2015); https://doi.org/10.1098/rspa.2015.0502
- Q. Zhang, K. De Oliveira Vigier, S. Royer and F. Jerome, Chem. Soc. Rev., 41, 7108 (2012); https://doi.org/10.1039/C2CS35178A
- A.P. Abbott, R.C. Harris, S. Ryder, C. D’Agostino, L.F. Gladden and M.D. Mantle, Green Chem., 13, 82 (2011); https://doi.org/10.1039/C0GC00395F
- D. Carriazo, M.C. Serrano, M.C. Gutiérrez, M.L. Ferrer and F. del Monte, Chem. Soc. Rev., 41, 4996 (2012); https://doi.org/10.1039/c2cs15353j
- C. Ruß and B. König, Green Chem., 14, 2969 (2012); https://doi.org/10.1039/c2gc36005e
- M. Francisco, A. van den Bruinhorst and M.C. Kroon, Angew. Chem. Int. Ed., 52, 3074 (2013); https://doi.org/10.1002/anie.201207548
- D. Reinhardt, F. Ilgen, D. Kralisch, B. Konig and G. Kreisel, Green Chem., 10, 1170 (2008); https://doi.org/10.1039/b807379a
- E.L. Smith, A.P. Abbott and K.S. Ryder, Chem. Rev., 114, 11060 (2014); https://doi.org/10.1021/cr300162p
- M. Zdanowicz, K. Wilpiszewska and T. Spychaj, Carbohydr. Polym., 200, 361 (2018); https://doi.org/10.1016/j.carbpol.2018.07.078
- A.E. Ünlü, A. Arikaya and S. Takaç, Green Process. Synth., 8, 355 (2018); https://doi.org/10.1515/gps-2019-0003
- Y. Dai, J. van Spronsen, G.-J. Witkamp, R. Verpoorte and Y. Haehoi, Anal. Chim. Acta, 766, 61 (2013); https://doi.org/10.1016/j.aca.2012.12.019
- P. Xu, G.-W. Zheng, M.-H. Zong, N. Li andW.-Y. Lou, Bioresour. Bioprocess., 4, 34 (2017); https://doi.org/10.1186/s40643-017-0165-5
- S. Sarmad, J.-P. Mikkola and X. Ji, ChemSusChem, 10, 324 (2017); https://doi.org/10.1002/cssc.201600987
- N. Rameshkumar, A. Veena, R. Ilavarasan, P. Shanmugapandiyan, M. Adiraj and S.K. Sridhar, Biol. Pharm. Bull., 26, 188 (2003); https://doi.org/10.1248/bpb.26.188
- D.B. Lovejoy and D.R. Richardson, Blood, 100, 666 (2002); https://doi.org/10.1182/blood.V100.2.666
- M. Hong, H. Yin, D. Wang and Z. Gao, Acta Crystallogr. Sect. E Struct. Rep. Online, 61, m801 (2005); https://doi.org/10.1107/S1600536805009694
- F. Ilgena and B. König, Green Chem., 11, 848 (2009); https://doi.org/10.1039/B816551C
- R. EI-Sayed, Indian J. Chem., 45B, 738 (2006).
- G. Imperato, E. Eibler, J. Niedermaier and B. König, Chem. Commun., 1170 (2005); https://doi.org/10.1039/B414515A
- T. Steiner, N. Veldman, A.M.M. Schreurs, J. Kanters and J. Kroon, J. Mol. Struct., 447, 39 (1998); https://doi.org/10.1016/S0022-2860(98)00299-3
- K. Colanceska-Ragenovic, V. Dimova, V. Kakurinov, D. Molnar and A. Buzarovska, Molecules, 6, 815 (2001); https://doi.org/10.3390/61000815
- V. Krishnakumar, N.G. Vindhya, B.K. Mandal and F.-R.N. Khan, Ind. Eng. Chem. Res., 53, 10814 (2014); https://doi.org/10.1021/ie501320a
- Q. Zhang, K. De Oliveira Vigier, S. Royer and F. Jérôme, Chem. Soc. Rev., 41, 7108 (2012); https://doi.org/10.1039/c2cs35178a
- P. Liu, J.-W. Hao, L.-P. Mo and Z.-H. Zhang, RSC Adv., 5, 48675 (2015); https://doi.org/10.1039/C5RA05746A
- A. Paiva, R. Craveiro, I. Aroso, M. Martins, R.L. Reis and A.R.C. Duarte, ACS Sustain. Chem. Eng., 2, 1063 (2014); https://doi.org/10.1021/sc500096j
- C. Ramalingan,Y.T. Park and S. Kabilan, Eur. J. Med. Chem., 41, 683 (2006); https://doi.org/10.1016/j.ejmech.2006.02.005
- S. Balasubramanian, G. Aridoss, P. Parthiban, C. Ramalingan and S. Kabilan, Biol. Pharm. Bull., 29, 125 (2006); https://doi.org/10.1248/bpb.29.125
- M. Srinivasan, S. Perumal and S. Selvaraj, Chem. Pharm. Bull. (Tokyo), 54, 795 (2006); https://doi.org/10.1248/cpb.54.795
- A. Manimekalai, J. Jayabharathi, L. Rufina and R. Mahendhiran, Indian J. Chem., 42B, 2074 (2003)
- C.R. Noller and V. Baliah, J. Am. Chem. Soc., 70, 3853 (1948); https://doi.org/10.1021/ja01191a092
- S. Savithiri, M. Arockia doss, G. Rajarajan and V. Thanikachalam, J. Mol. Struct., 1075, 430 (2014); https://doi.org/10.1016/j.molstruc.2014.06.096
- R. Revathi, R.V. Perumal, K.S.R. Pai, G. Arunkumar, D. Sriram and S. Kini, Drug Design Dev. Ther., 2015, 3779 (2015); https://doi.org/10.2147/DDDT.S83047
References
T. Welton, Proc. Math Phys. Eng. Sci., 471, 20150502 (2015); https://doi.org/10.1098/rspa.2015.0502
Q. Zhang, K. De Oliveira Vigier, S. Royer and F. Jerome, Chem. Soc. Rev., 41, 7108 (2012); https://doi.org/10.1039/C2CS35178A
A.P. Abbott, R.C. Harris, S. Ryder, C. D’Agostino, L.F. Gladden and M.D. Mantle, Green Chem., 13, 82 (2011); https://doi.org/10.1039/C0GC00395F
D. Carriazo, M.C. Serrano, M.C. Gutiérrez, M.L. Ferrer and F. del Monte, Chem. Soc. Rev., 41, 4996 (2012); https://doi.org/10.1039/c2cs15353j
C. Ruß and B. König, Green Chem., 14, 2969 (2012); https://doi.org/10.1039/c2gc36005e
M. Francisco, A. van den Bruinhorst and M.C. Kroon, Angew. Chem. Int. Ed., 52, 3074 (2013); https://doi.org/10.1002/anie.201207548
D. Reinhardt, F. Ilgen, D. Kralisch, B. Konig and G. Kreisel, Green Chem., 10, 1170 (2008); https://doi.org/10.1039/b807379a
E.L. Smith, A.P. Abbott and K.S. Ryder, Chem. Rev., 114, 11060 (2014); https://doi.org/10.1021/cr300162p
M. Zdanowicz, K. Wilpiszewska and T. Spychaj, Carbohydr. Polym., 200, 361 (2018); https://doi.org/10.1016/j.carbpol.2018.07.078
A.E. Ünlü, A. Arikaya and S. Takaç, Green Process. Synth., 8, 355 (2018); https://doi.org/10.1515/gps-2019-0003
Y. Dai, J. van Spronsen, G.-J. Witkamp, R. Verpoorte and Y. Haehoi, Anal. Chim. Acta, 766, 61 (2013); https://doi.org/10.1016/j.aca.2012.12.019
P. Xu, G.-W. Zheng, M.-H. Zong, N. Li andW.-Y. Lou, Bioresour. Bioprocess., 4, 34 (2017); https://doi.org/10.1186/s40643-017-0165-5
S. Sarmad, J.-P. Mikkola and X. Ji, ChemSusChem, 10, 324 (2017); https://doi.org/10.1002/cssc.201600987
N. Rameshkumar, A. Veena, R. Ilavarasan, P. Shanmugapandiyan, M. Adiraj and S.K. Sridhar, Biol. Pharm. Bull., 26, 188 (2003); https://doi.org/10.1248/bpb.26.188
D.B. Lovejoy and D.R. Richardson, Blood, 100, 666 (2002); https://doi.org/10.1182/blood.V100.2.666
M. Hong, H. Yin, D. Wang and Z. Gao, Acta Crystallogr. Sect. E Struct. Rep. Online, 61, m801 (2005); https://doi.org/10.1107/S1600536805009694
F. Ilgena and B. König, Green Chem., 11, 848 (2009); https://doi.org/10.1039/B816551C
R. EI-Sayed, Indian J. Chem., 45B, 738 (2006).
G. Imperato, E. Eibler, J. Niedermaier and B. König, Chem. Commun., 1170 (2005); https://doi.org/10.1039/B414515A
T. Steiner, N. Veldman, A.M.M. Schreurs, J. Kanters and J. Kroon, J. Mol. Struct., 447, 39 (1998); https://doi.org/10.1016/S0022-2860(98)00299-3
K. Colanceska-Ragenovic, V. Dimova, V. Kakurinov, D. Molnar and A. Buzarovska, Molecules, 6, 815 (2001); https://doi.org/10.3390/61000815
V. Krishnakumar, N.G. Vindhya, B.K. Mandal and F.-R.N. Khan, Ind. Eng. Chem. Res., 53, 10814 (2014); https://doi.org/10.1021/ie501320a
Q. Zhang, K. De Oliveira Vigier, S. Royer and F. Jérôme, Chem. Soc. Rev., 41, 7108 (2012); https://doi.org/10.1039/c2cs35178a
P. Liu, J.-W. Hao, L.-P. Mo and Z.-H. Zhang, RSC Adv., 5, 48675 (2015); https://doi.org/10.1039/C5RA05746A
A. Paiva, R. Craveiro, I. Aroso, M. Martins, R.L. Reis and A.R.C. Duarte, ACS Sustain. Chem. Eng., 2, 1063 (2014); https://doi.org/10.1021/sc500096j
C. Ramalingan,Y.T. Park and S. Kabilan, Eur. J. Med. Chem., 41, 683 (2006); https://doi.org/10.1016/j.ejmech.2006.02.005
S. Balasubramanian, G. Aridoss, P. Parthiban, C. Ramalingan and S. Kabilan, Biol. Pharm. Bull., 29, 125 (2006); https://doi.org/10.1248/bpb.29.125
M. Srinivasan, S. Perumal and S. Selvaraj, Chem. Pharm. Bull. (Tokyo), 54, 795 (2006); https://doi.org/10.1248/cpb.54.795
A. Manimekalai, J. Jayabharathi, L. Rufina and R. Mahendhiran, Indian J. Chem., 42B, 2074 (2003)
C.R. Noller and V. Baliah, J. Am. Chem. Soc., 70, 3853 (1948); https://doi.org/10.1021/ja01191a092
S. Savithiri, M. Arockia doss, G. Rajarajan and V. Thanikachalam, J. Mol. Struct., 1075, 430 (2014); https://doi.org/10.1016/j.molstruc.2014.06.096
R. Revathi, R.V. Perumal, K.S.R. Pai, G. Arunkumar, D. Sriram and S. Kini, Drug Design Dev. Ther., 2015, 3779 (2015); https://doi.org/10.2147/DDDT.S83047