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Amidation of benzoyl chloride with morpholine; 1-benzoylmorpholine

SyntheticPage 650
DOI: 10.1039/SP650
Submitted Jul 23, 2013, published Jul 24, 2013
Lihong Li (Lihongli0707@yahoo.com), Pratik Gurnani (pratik.gurnani@warwick.ac.uk)
A contribution from Scott group, Warwick University


			Reaction Scheme: <IMG src="/images/empty.gif"><IMG alt="" src="/images/empty.gif">Amidation of <SPAN id=csm1374845516434 class=csm-chemical-name title="benzoyl chloride">benzoyl chloride</SPAN> with <SPAN id=csm1374845524243 class="csm-chemical-name csm-not-validated" title=morpholine>morpholine</SPAN><IMG alt="" src="/images/empty.gif"><IMG src="/images/empty.gif">

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