Amidation of benzoyl chloride with morpholine
SyntheticPage 650
DOI:
Submitted: July 23, 2013, published: July 24, 2013
Authors
Lihong Li (Lihongli0707@yahoo.com)
Pratik Gurnani (pratik.gurnani@warwick.ac.uk)
A contribution from

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