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N-Benzyl-3-(2-morpholine)ethoxy-5-methoxy benzofuran-2-carboxamide

Department of Medicinal Chemistry, Victorian College of Pharmacy (Monash University), 381 Royal Parade Parkville, Victoria 3052, Australia
Molecules 2001, 6(3), M199; https://doi.org/10.3390/M199
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)
As part of a research programme targeting novel indole-like molecules as potential cannabinoid agonists [1,2,3,4] we synthesised methyl 3-(2-(N-morpholino)ethyl-5-methoxybenzofuran-2-carboxylate.
Molecules 06 m199 i001
5-Methoxy-3-(2-ethyl morpholine) benzofuran-2-carboxylic acid (50.0 mg, 0.15 mmol) and benzylamine (18.2 mg, 0.17 mmol) and TBTU (55.0 mg, 0.17 mmol) were dissolved in anhydrous DMF (3.0 mL) and to this stirring solution was added DIPEA (33.0 mL, 0.19 mmol). The solution was stirred at room temperature under an atmosphere of nitrogen for 3.0 hours. The DMF was evaporated under reduced pressure and water was added and the aqueous layer was extracted with ethyl acetate. The organic layers were dried over magnesium sulphate, filtered and evaporated under reduced pressure to afford the desired benzofuran-2-carboxamide as an orange gum. This was further purified by column chromatography eluting with (chloroform/methanol) (99/1) to afford (21.39 mg, 33.5 %) of the desired N-benzyl-3-(2-morpholine)ethoxy-5-methoxy benzofuran-2-carboxamide as yellow crystals
M.p. 118-120 °C.
MS : 411 (M+1).+.
IR: 3100, 3000, 1660, 1600, 1500, 1450, 1400, 1300, 1290, 1105, 1100, 1030, 1050, 870, 750.
1H NMR (300 MHz, DMSO-d6): 2.35 (m, 3H, CH2 +CH), 2.65 (m, 2H, CH2), 3.40 (m, 2H, 2 x CH2), 3.81 (d, J = 4.2 Hz, 2H, NHCH2), 4.03 (3H, s, OCH3), 4.53 (m, 3H, CH2 + CH), 7.06 (dd, J = 2.2, J = 6.4 Hz, 1H, H-6), 7.24 (d, J = 2.67 Hz, 1H, H-4), 7.49 (d, J = 9.0 Hz, 1H, H-7), 8.56 (m, 1H, NH).
HPLC retention time = 8.87 minutes, Gradient conditions 30 B/70 A to 90 B/10 A over 20 minutes a (B = 90 % CH3CN, 10 % H2O)/ (A = 0.1 % TFA in H2O) using Zorbax 4.6 mm x 250 mm.

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. N-Benzyl-3-(2-morpholine)ethoxy-5-methoxy benzofuran-2-carboxamide. Molecules 2001, 6, M199. https://doi.org/10.3390/M199

AMA Style

Moloney GP. N-Benzyl-3-(2-morpholine)ethoxy-5-methoxy benzofuran-2-carboxamide. Molecules. 2001; 6(3):M199. https://doi.org/10.3390/M199

Chicago/Turabian Style

Moloney, Gerard P. 2001. "N-Benzyl-3-(2-morpholine)ethoxy-5-methoxy benzofuran-2-carboxamide" Molecules 6, no. 3: M199. https://doi.org/10.3390/M199

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