Amidation of benzoyl chloride with morpholine; 1-benzoylmorpholine
SyntheticPage 650
DOI:
10.1039/SP650
Submitted Jul 23, 2013, published Jul 24, 2013
Chemicals Used
Morpholine (Aldrich)
Triethylamine (Fisher Scientific)
Dichloromethane (Fisher Scientific)
Benzoyl chloride (Aldrich)
Procedure
To a stirred solution of morpholine (0.958 g, 11.0 mmol) and triethylamine (1.260 g, 12.0 mmol) in dichloromethane (20 mL) at ambient temperature was carefully added benzoyl chloride (1.406 g, 10.0 mol) at a sufficiently slow rate that boiling of the solvent is minimized. The viscous dark reaction mixture was stirred for a further 1 h before water (20 mL) was added. The dichloromethane extracts (3 x 10 mL) were washed with water (4 x 15 mL) and dried over sodium sulfate. The volatiles were removed under pressured to leave an off-white product. (1.82 g, 95 %).
Author's Comments
Worked well first time and was reproducible. Take care with the addition.
Data
1H NMR (300 MHz, CDCl3): 7.21-7.40 (m, 5 H, ArH), 3.50 (br, s, 6H, CH2), 3.29 (br, s, 2H, CH2 ).
13C{1H}NMR (75.5 MHz, CDCl3): 169.8 (CH=O), 134.7 (Ar-Cq), 129.3 (Ar-CH), 128.0 (Ar-CH), 126.5 (Ar-CH), 76.6 (CH2), 74.0 (CH2), 66.3 (CH2).
MS (ESI): m/z 191.0 (M+H)+
Anal. Found (calculated for C10H8N2O): C 69.47 (69.09). H 6.48 (6.85), N 7.02 (7.32)%.
Lead Reference
S. Rubino, S. Petruso, R. Pierattelli, G. Bruno, G. C. Stocco, L. Steardo, M. Motta, M. Passerotto, E. Del Giudice and G. Guli,
J. Inorg. Biochem., 2004,
98, 2071-2079.
http://dx.doi.org/10.1016/j.jinorgbio.2004.09.012
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Keywords: acyl chloride, addition, amidation, amines, aromatics/arenes, ethers