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• W2012516303 abstract "first_page settings Order Article Reprints Font Type: Arial Georgia Verdana Font Size: Aa Aa Aa Line Spacing:    Column Width:    Background: Open AccessShort Note N-(2-Ethylmorpholino)-3-bis-keto(1-naphthyl)oxindole by Gerard P. Moloney Department of Medicinal Chemistry, Victorian College of Pharmacy (Monash University), 381 Royal Parade Parkville, Victoria 3052, Australia Molecules 2001, 6(3), M196; https://doi.org/10.3390/M196 Received: 4 September 2000 / Accepted: 29 September 2000 / Published: 25 March 2001 (This article belongs to the Section Molbank Section of Molecules, 1997-2001) Download Download PDF Download PDF with Cover Download XML Download Epub Download Supplementary Material Versions Notes As part of a research programme targeting novel indole-like molecules as potential cannabinoid agonists [1,2,3,4] we synthesised N-(2-ethylmorpholino)-3-bis-keto(1-naphthyl)oxindole.N-(ethylmorpholine) oxindole (409.0 mg, 1.66 mmol) was dissolved in anhydrous THF (25.0 mL) and the reaction mixture was cooled to -78 °C then HMPA (868.0 mL, 4.99 mmol) was added followed by KHMDS (3.66 mL, 1.83 mmol) being added dropwise. The solution was stirred for 30 minutes at -22 °C then cooled to -78 °C after which 1-naphthyl chloride (475.0 mg, 2.49 mmol) was added. The reaction was allowed to stir up to room temperature overnight. The solvent was evaporated under reduced pressure and water was added and the aqueous phase was extracted with ethyl acetate, dried over magnesium sulphate, filtered, and evaporated under reduced pressure to afford (552.5 mg, 60.0 %) of the undesired N-(ethylmorpholine)-3-bis keto(-1-naphthyl) oxindole as a yellow powder.M.p. 80-85 °C.MS: 555 (M+1)+..IR: 3080, 1800, 1600, 1420, 1300, 1110, 1100, 950, 700.1H NMR (300 MHz, CDCl3): 2.55 (m, 4H, 2 x CH2), 2.66 (t, J = 6.9 Hz, 2H, CH2), 3.71 (m, 4H, 2 x CH2) 3.93 (t, J = 6.9 Hz, 2H, CH2), 6.07 (m, 1H, ArH), 6.59 (dd, J = 0.9 Hz, J = 7.5 Hz, 1H, ArH), 6.86 (d, J = 7.8 Hz, 1H, ArH), 7.15 (m, 1H, ArH), 7.55 (m, 5H, 5 x ArH), 7.85-8.13 (m, 6H, 6 x ArH), 8.28 (m, 1H, ArH), 8.53 (m, 1H, ArH), 8.95 (m, 1H, ArH).Anal. calcd. for C36H30N2O4 C 77.96, 5.45: Found C 77.65, H 5.50. Supplementary materialsSupplementary File 1Supplementary File 2ReferencesWard, S. J.; Mastriani, D.; Casiano, F.; Arnold, R. J. Pharmacol. Exp. 1990, 255, 1230–1239. Bell, M. R.; D'Ambra, T. E.; Kumar, V.; Eissenstat, M. A.; Herrmann, J. L.; Wetzel, J. R.; Rosi, D.; Philion, R. E.; Daum, S. J.; Hlasta, D. J.; Kullnig, R. K.; Ackerman, J. H.; Haubrich, D. R.; Luttinger, D. A.; Baizman, E. R.; Miller, M. S.; Ward, S. J. J. Med. Chem. 1991, 34, 1099–1110. [CrossRef] Ward, S. J.; Miller, M. S.; Luttinger, D. A.; Eissenstat, M. A.; Bell, M. R. Neurosci. Abstr. 1988, 14, 324. D'Ambra, T. E.; Estep, K. G.; Bell, M. R.; Eissenstat, M. A.; Josef, K. A.; Ward, S. J.; Haycock, D. A.; Baizman, E. R.; Casiano, F. M.; Belgin, N. C.; Chippari, S. M.; Grego, J. D.; Kullnig, R. K.; Daley, G. T. J. Med. Chem. 1992, 35, 124–135. [CrossRef] Sample availability: available from the authors and MDPI. © 2001 MDPI. All rights reserved. Molecules website www.mdpi.org/molecules/ Share and Cite MDPI and ACS Style Moloney, G.P. N-(2-Ethylmorpholino)-3-bis-keto(1-naphthyl)oxindole. Molecules 2001, 6, M196. https://doi.org/10.3390/M196 AMA Style Moloney GP. N-(2-Ethylmorpholino)-3-bis-keto(1-naphthyl)oxindole. Molecules. 2001; 6(3):M196. https://doi.org/10.3390/M196 Chicago/Turabian Style Moloney, Gerard P. 2001. N-(2-Ethylmorpholino)-3-bis-keto(1-naphthyl)oxindole Molecules 6, no. 3: M196. https://doi.org/10.3390/M196 Find Other Styles Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here. Article Metrics No No Article Access Statistics For more information on the journal statistics, click here. Multiple requests from the same IP address are counted as one view." @default.
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