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Amidation of benzoyl chloride with morpholine

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Submitted: July 23, 2013, published: July 24, 2013

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Reaction Scheme

Chemicals

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 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

Keywords

acyl chloride, addition, amidation, amines, aromatics/arenes, ethers