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Short Note

4-Dodecyl-6-methyl-2-morpholone

by
Bohumil Steiner Steiner
,
Jan Gajdos
,
Miroslav Koos
* and
Bjørnar Hassel
Institute of Chemistry, Slovak Academy of Sciences, Dubravska cesta 9, SK-84238 Bratislava, Slovak Republic
*
Author to whom correspondence should be addressed.
Molecules 1997, 2(11), M42; https://doi.org/10.3390/M42
Submission received: 28 October 1997 / Published: 18 November 1997
(This article belongs to the Section Molbank Section of Molecules, 1997-2001)
Versions Notes
Molecules 02 m42 i001
2-Morpholones may be synthesized from the corresponding beta-amino alcohols by heating with an alpha-halo ester [1]. Several alternative methods have also been described [2].
1-Dodecylamino-2-propanol (4.86 g, 20 mmol) was added to a stirred suspension of NaH (0.52 g, 21.5 mmol) in dry benzene (20 ml). The resulting mixture was cooled (ice) and ethyl chloroacetate (2.45 g, 20 mmol) was added during 15 min followed by stirring at room temperature for 1 h and for an additional 1h under reflux. After cooling, ether (50 ml) was added and the mixture was washed with 2 N HCl and water. The organic layer was dried and the solvent evaporated to give a crude product. Recrystallization from hexane afforded the title compound (2.6 g, 46%) as white crystals.
M.p. 37-39 deg.C.
TLC (Hexane/EtOAc 2:1): Rf 0.25.
1H-NMR (CDCl3): 4.18 (ABq, J=16.5 Hz, 2H, H-2); 3.87 (m, J=9.8 and 6.3 and 3.3 Hz, 1H, H-6); 3.40 (m, 1H, CH2N); 3.31 (m, 1H, CH2N); 3.25 (dd, J=12.0 and 9.8 Hz, 1H, H-5); 3.12 (dd, J=12.0 and 3.3 Hz, 1H, H-5'); 1.54 (m, 2H, CH2CH2N); 1.27 (d, J=6.3 Hz, 3H, CH3); 1.26 (s, 18H, 9 x CH2); 0.88 (t, J=6.4 Hz, 3H, CH3).
13C-NMR (CDCl3): 166.5 (C=O), 69.6 (C-6), 67.8 (C-2), 52.4 (C-5), 46.5 (CH2N), 31.9, 29.6, 29.4, 26.9, 22.7 (the other CH2 groups), 18.3 (CH3 at C-6), 14.1 (CH3).
Anal. calc. for C17H33NO2 (283.45): C 72.04, H 11.73, N 4.94; found: C 72.19, H 11.82, N 4.90.

Supplementary materials

Supplementary File 1Supplementary File 2

Acknowledgments

The authors would like to thank Scientific Grant Agency (VEGA, project No. 2/4144/97) for financial support.

References and Notes

  1. Clarke, F. H. J. Org. Chem. 1962, 27, 3251.
  2. Sainsbury, M. Coffey, S., Ed.; Rodd's Chemistry of Carbon Compounds; Volume IV, Part H; Elsevier: Amsterdam, 1978; p. 427. [Google Scholar]
  • Sample Availability: Available from the authors and MDPI, MDPI Reg. No.13732.

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MDPI and ACS Style

Steiner, B.S.; Gajdos, J.; Koos, M.; Hassel, B. 4-Dodecyl-6-methyl-2-morpholone. Molecules 1997, 2, M42. https://doi.org/10.3390/M42

AMA Style

Steiner BS, Gajdos J, Koos M, Hassel B. 4-Dodecyl-6-methyl-2-morpholone. Molecules. 1997; 2(11):M42. https://doi.org/10.3390/M42

Chicago/Turabian Style

Steiner, Bohumil Steiner, Jan Gajdos, Miroslav Koos, and Bjørnar Hassel. 1997. "4-Dodecyl-6-methyl-2-morpholone" Molecules 2, no. 11: M42. https://doi.org/10.3390/M42

APA Style

Steiner, B. S., Gajdos, J., Koos, M., & Hassel, B. (1997). 4-Dodecyl-6-methyl-2-morpholone. Molecules, 2(11), M42. https://doi.org/10.3390/M42

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