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(4R)-1'-Acetyl-2,3-O-isopropylidene-methylspiro [4,6-dideoxy-ß-D-ribo-hexopyranosid-4,5'-imidazolidin]-2',4'-dione
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Marina A. Tlekhusezh
Roman V. Makuilov
Larisa A. Badovskaya
Research Laboratory of Furan Chemistry, Kuban State Technological University, Moskovskaya st. 2, Krasnodar, 350072, Russian Federation
Author to whom correspondence should be addressed.
Molecules 2000, 5(2), M141;
Submission received: 1 February 2000 / Accepted: 8 February 2000 / Published: 23 February 2000
(This article belongs to the Section Molbank Section of Molecules, 1997-2001)
Molecules 05 m141 i001
The title compound was synthesized by the reaction of N-benzyl-3-benzylamino-4-hydroxybutanamide with 3-pyridinecarboxaldehyde using the procedure described in [1]. A mixture of N-benzyl-3-benzylamino-4-hydroxybutanamide (2.98 g, 0.01 mol), 3-pyridinecarboxaldehyde (nicotinaldehyde) (1.02 g, 0.01 mol), molecular sieves (Na-A, 20 g), p-TsOH (0.02 g) and dry chloroform (50 ml) was heated to reflux for 4 h. The reaction mixture was then filtered, and the solvent was evaporated. The residue was dissolved in ethyl acetate (10 ml) and cooled to 0 °C for crystallization of desired product. The crystals obtained was separated with filtration and recrystallized from ethanol to yield 3.33 g (86 %) of 3-benzyl-4-(N-benzylcarbamoylmethyl)-2-(3-pyridyl)-1,3-oxazolidine.
M.p. 93 °C (ethanol)
IR (vaseline oil, cm-1): 3310 (N-H); 1650 (C=O); 1550 (N-H); 1605 (C=C).
1H NMR (CDCl3, 250 MHz): 2.25, 2.31 (dd, dd, 2H, CH2CO, J = 16.0 Hz); 2.41, 2.51 (d, d, 2H, NCH2, J = 14.0 Hz); 3.5 (m, 1H, NCH); 4.07, 4.26 (dd, dd, 2H, OCH2); 6.23 (broad s, 1H, NH); 7.18 (m, 11H, Ph, 5-H Py); 7.72 (dd, 1H, 6-H Py); 8.20 (dd, dd, 2H, NHCH2}, 8,50 (dd, 2H, 2,4-H Py).
Anal. calcd. for C24H25N3O2 (387.48): C 74.51; H 6.62; N 10.78; Found: C 74.39; H 6.50; N 10.85.

Supplementary materials

Supplementary File 1Supplementary File 2


  1. Tlekhusezh, M.A.; Badovskaya, L.A.; Tyukhteneva, Z.I. Khimiya geterotsikl. Soedin. (Chemistry of Hetrocyclic compounds, Russia). 1996, 5, 711–716. [Google Scholar]
  • Sample availability: Available from authors and MDPI.

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MDPI and ACS Style

Tlekhusezh, M.A.; Makuilov, R.V.; Badovskaya, L.A. 3-Benzyl-4-(N-benzylcarbamoylmethyl)-2-(3-pyridyl)-1,3-oxazolidine. Molecules 2000, 5, M141.

AMA Style

Tlekhusezh MA, Makuilov RV, Badovskaya LA. 3-Benzyl-4-(N-benzylcarbamoylmethyl)-2-(3-pyridyl)-1,3-oxazolidine. Molecules. 2000; 5(2):M141.

Chicago/Turabian Style

Tlekhusezh, Marina A., Roman V. Makuilov, and Larisa A. Badovskaya. 2000. "3-Benzyl-4-(N-benzylcarbamoylmethyl)-2-(3-pyridyl)-1,3-oxazolidine" Molecules 5, no. 2: M141.

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