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Short Note

[5-Hydroxy-1-(2-morpholinoethyl)-1H-indol-3-yl](4-methoxyphenyl)methanone

by
Gerard P. Moloney
Department of Medicinal Chemistry, Victorian College of Pharmacy (Monash University) 381 Royal Parade Parkville Vic 3052 Australia
Molecules 2001, 6(3), M194; https://doi.org/10.3390/M194
Submission received: 4 September 2000 / Accepted: 29 September 2000 / Published: 25 March 2001
(This article belongs to the Section Molbank Section of Molecules, 1997-2001)
Versions Notes
As part of a research programme targeting novel indole-based molecules as potential cannabinoid agonists we synthesised [5-hydroxy-1-(2-morpholinoethyl)-1H-indol-3-yl](4-methoxyphenyl)methanone [1,2,3,4].
Molecules 06 m194 i001
N-(3-ethylmorpholine)-5-methoxy indole (160 mg, 0.61 mmol) was dissolved in anhydrous dichloromethane (5.0 mL) and 4-methoxy benzoyl chloride (125.5 mg, 0.74 mmol) was added and the reaction mixture was stirred at room temperature under an atmosphere of nitrogen and aluminium chloride (204.3 mg, 1.5 mmol) was added gradually. The reaction mixture was stirred for 1 hour at room temperature. Water was added and the solution was extracted with ethyl acetate, dried over magnesium sulphate, filtered and evaporated under reduced pressure to afford a residue which was purified by column chromatography eluting with chloroform then chloroform/methanol (99/1) to afford (85.0 mg, 35.1 %) of the desired [5-Hydroxy-1-(2-morpholinoethyl)-1H-indol-3-yl](4-methoxyphenyl)methanone as a soft yellow solid.
MS : 396 (M + 1)+..
IR: 3000, 1600, 1490, 1450, 1400, 1390, 1340, 1300, 1050, 880, 820, 800, 790, 770, 750, 670.
1H NMR (300 MHz, DMSO-d6): 2.42 (m, 4H, 2 x CH2), 2.68 (t, J = 6.0 Hz, 2H, CH2), 3.50 (m, 5H, 2 x CH2, CH), 3.84 (s, 3H, OCH3), 3.85 (s, 3H, OCH3), 4.36 (t, J = 6.0 Hz, 1H, CH), 6.81 (d, J = 9.0 Hz, 1H, ArH), 7.03 (d, J = 8.7 Hz, 2H, 2 x ArH), 7.93 (d, J = 8.7 Hz, 2H, 2 x ArH), 8.0 (d, J = 9.0 Hz, 1H, ArH), 8.15 (s, 1H, ArH).
Exact mass : C23H26N2O4 requires (M)+. = 394.18925, Found (M)+. = 394.19002.

Supplementary materials

Supplementary File 1Supplementary File 2

References

  1. Ward, S. J.; Mastriani, D.; Casiano, F.; Arnold, R. J. Pharmacol. Exp. 1990, 255, 1230–1239.
  2. 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. [PubMed]
  3. Ward, S. J.; Miller, M. S.; Luttinger, D. A.; Eissenstat, M. A.; Bell, M. R. Neurosci. Abstr. 1988, 14, 324.
  4. 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. [PubMed]
  • Sample availability: available from the authors and MDPI.

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MDPI and ACS Style

Moloney, G.P. [5-Hydroxy-1-(2-morpholinoethyl)-1H-indol-3-yl](4-methoxyphenyl)methanone. Molecules 2001, 6, M194. https://doi.org/10.3390/M194

AMA Style

Moloney GP. [5-Hydroxy-1-(2-morpholinoethyl)-1H-indol-3-yl](4-methoxyphenyl)methanone. Molecules. 2001; 6(3):M194. https://doi.org/10.3390/M194

Chicago/Turabian Style

Moloney, Gerard P. 2001. "[5-Hydroxy-1-(2-morpholinoethyl)-1H-indol-3-yl](4-methoxyphenyl)methanone" Molecules 6, no. 3: M194. https://doi.org/10.3390/M194

APA Style

Moloney, G. P. (2001). [5-Hydroxy-1-(2-morpholinoethyl)-1H-indol-3-yl](4-methoxyphenyl)methanone. Molecules, 6(3), M194. https://doi.org/10.3390/M194

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