3-(Trifluoromethyl)benzylamine → N-(3-(trifluoromethyl)benzyl)-2-(2-nitro-5-(piperidin-1-yl)phenyl)-isonicotinamide

HRID 1407974Notes

Reaction equation

[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)=[CH:6][C:5]=1[C:16]1[CH:17]=[C:18]([CH:22]=[CH:23][N:24]=1)[C:19](O)=[O:20])([O-:3])=[O:2].CCN=C=NCCCN(C)C.Cl.[F:37][C:38]([F:48])([F:47])[C:39]1[CH:40]=[C:41]([CH2:45][NH2:46])[CH:42]=[CH:43][CH:44]=1>ClCCl.CN(C)C1C=CN=CC=1>[F:37][C:38]([F:47])([F:48])[C:39]1[CH:40]=[C:41]([CH:42]=[CH:43][CH:44]=1)[CH2:45][NH:46][C:19](=[O:20])[C:18]1[CH:22]=[CH:23][N:24]=[C:16]([C:5]2[CH:6]=[C:7]([N:10]3[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]3)[CH:8]=[CH:9][C:4]=2[N+:1]([O-:3])=[O:2])[CH:17]=1

Participants

Conditions

Temperature: 25 °C

Procedure

Into a 50-mL round bottom flask, was placed a solution of 2-(2-nitro-5-(piperidin-1-yl)phenyl)isonicotinic acid (1 g, 3.06 mmol, 1.00 equiv) in dichloromethane (20 mL), EDC.HCl (970 mg, 5.05 mmol, 1.65 equiv), 4-dimethylaminopyridine (620 mg, 5.08 mmol, 1.66 equiv), and (3-(trifluoromethyl)phenyl)methanamine (590 mg, 3.37 mmol, 1.10 equiv). The resulting solution was stirred overnight at 25° C. in an oil bath. The reaction progress was monitored by LCMS. The mixture was concentrated under vacuum. The residue was applied onto a silica gel column and eluted with petroleum ether/ethyl acetate (10:1˜3:1). This resulted in 800 mg (51%) of N-(3-(trifluoromethyl)benzyl)-2-(2-nitro-5-(piperidin-1-yl)phenyl)isonicotinamide as a yellow solid.

Workup

customInto a 50-mL round bottom flask, was placed
concentrationThe mixture was concentrated under vacuum
washeluted with petroleum ether/ethyl acetate (10:1˜3:1)
customThis resulted in 800 mg (51%) of N-(3-(trifluoromethyl)benzyl)-2-(2-nitro-5-(piperidin-1-yl)phenyl)isonicotinamide as a yellow solid

Sources & evidence

ORD record: ord-42175af05c024b2b8e37d416fa454c2f
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08916569B2

Reaction notes

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