3-(Trifluoromethyl)benzylamine → N-(3-(trifluoromethyl)benzyl)-2-chloroisonicotinamide
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][N:10]=1)[C:5]([OH:7])=O.[F:11][C:12]([F:22])([F:21])[C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH2:16][NH2:17].CCN=C=NCCCN(C)C.Cl>ClCCl.CN(C)C1C=CN=CC=1>[F:11][C:12]([F:21])([F:22])[C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH2:16][NH:17][C:5](=[O:7])[C:4]1[CH:8]=[CH:9][N:10]=[C:2]([Cl:1])[CH:3]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 25 °C
Procedure
Into a 500-mL round bottom flask, was placed a solution of 2-chloroisonicotinic acid (18 g, 113.92 mmol, 2.00 equiv) in dichloromethane (200 mL), 3-(trifluoromethyl)benzylamine (10 g, 57.14 mmol, 1.00 equiv), EDC.HCl (22 g, 115.18 mmol, 2.00 equiv), and 4-dimethylaminopyridine (14 g, 114.75 mmol, 2.00 equiv). The resulting solution was stirred for 3 h at 25° C. The resulting solution was diluted with 500 mL of dichloromethane. The resulting mixture was washed with 2×50 mL of aqueous NH4Cl, 1×50 mL of 10% sodium bicarbonate, and 1×50 mL of brine. The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column and eluted with petroleum ether/ethyl acetate (5:1). The product was obtained as 11.8 g (63%) of a white solid.
Workup
- customInto a 500-mL round bottom flask, was placed
- washThe resulting mixture was washed with 2×50 mL of aqueous NH4Cl, 1×50 mL of 10% sodium bicarbonate, and 1×50 mL of brine
- dry with materialThe mixture was dried over anhydrous sodium sulfate
- concentrationconcentrated under vacuum
- washeluted with petroleum ether/ethyl acetate (5:1)
Sources & evidence
- ORD record
- ord-275f1c2522d643ab87dbddfb5fa7a193
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08916569B2
Reaction notes
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