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Volumn 36, Issue 5, 2007, Pages 658-659

Efficient method for dehydration condensation using pyridine-3-carboxylic anhydride (3-PCA): Synthesis of carboxamides from nearly equimolar amounts of carboxylic acids and amines

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EID: 34250177215     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2007.658     Document Type: Article
Times cited : (7)

References (32)
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    • Typical experimental procedure for the preparation of 3-phenyl-N-(3-phenylpropyl)propanamide is shown in the following: To a stirred solution of 3-phenylpropionic acid (49.6 mg, 0.33 mmol) in CH 2Cl2 (1.5 mL) were successively added pyridine-3- carboxylic anhydride (75.4 mg) and DMAP (40.4 mg) at 0°C. After having been stirred for 10 min, a solution of 3-phenylpropylamine (40.6 mg, 0.30 mmol) in dichloromethane (1.5 mL) was added. After the reaction mixture was stirred for 1 h, it was quenched with saturated aqueous sodium hydrogencarbonate. The mixture was extracted with EtOAc. The organic layer was washed with saturated aqueous sodium hydrogencarbonate, 1 M hydrogen chloride (3 times, brine, dried over anhydrous Na2SO4, and evaporated. The crude product was purified by preparative TLC (hexane/EtOAc, 1/9) to afford 3-phenyl-N-(3- phenylpropyl)propanamide 75.9 mg, 95, as a white solid
    • 4, and evaporated. The crude product was purified by preparative TLC (hexane/EtOAc = 1/9) to afford 3-phenyl-N-(3- phenylpropyl)propanamide (75.9 mg, 95%) as a white solid.
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    • 1H NMR. It indicates that 1-phenylethyl-pyridine-3- carboxamide is transferred to aqueous layer by acidic workup.
    • 1H NMR. It indicates that 1-phenylethyl-pyridine-3- carboxamide is transferred to aqueous layer by acidic workup.


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