[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([OH:12])=O)=[CH:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.[CH:19]1([NH2:22])[CH2:21][CH2:20]1.C(N(CC)CC)C>C(Cl)Cl.O.CN(C)C=O>[CH:19]1([NH:22][C:10](=[O:12])[CH2:9][CH2:8][C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[CH2:21][CH2:20]1To a stirred solution of 3-(4-fluorophenyl)propionic acid (5 g, 31 mmoles) and 0.1 mL of dimethylformamide in 50 mL of anhydrous CH2Cl2 at 0° C. was added oxalyl chloride (2.84 mL, 32.6 mmoles) and the mixture was stirred for 1 hour at 0° C. and for 1 hour at room temperature. After cooling to 0° C. were added cyclopropylamine (2.6 mL, 37.2 mmoles) and triethylamine (6.5 mL, 46.5 mmoles), and the mixture was stirred for 1 hour while warming to room temperature gradually. Then water was added and the product was extracted with CH2Cl2. The extract was washed with water, dried over MgSO4 and evaporated to give a solide residue. It was recrystallized from CH2Cl2 and hexane to give 4.94 g of N-cyclopropyl-3-(4-fluorophenyl)propionamide.
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