Piperidine → N-(5-(3,4-dimethylphenyl)pyrimidin-2-yl)-2-nitro-5-(piperidin-1-yl)benzamide

HRID 2406089Notes

Reaction equation

Cl[C:2]1[CH:3]=[CH:4][C:5]([N+:25]([O-:27])=[O:26])=[C:6]([CH:24]=1)[C:7]([NH:9][C:10]1[N:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[C:18]([CH3:23])[CH:17]=2)=[CH:12][N:11]=1)=[O:8].[NH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1>CN(C)C=O>[CH3:23][C:18]1[CH:17]=[C:16]([C:13]2[CH:12]=[N:11][C:10]([NH:9][C:7](=[O:8])[C:6]3[CH:24]=[C:2]([N:28]4[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]4)[CH:3]=[CH:4][C:5]=3[N+:25]([O-:27])=[O:26])=[N:15][CH:14]=2)[CH:21]=[CH:20][C:19]=1[CH3:22]

Participants

Conditions

Temperature: 85 °C

Procedure

Into a 50-mL round-bottom flask, was placed a solution of 5-chloro-N-(5-(3,4-dimethylphenyl)pyrimidin-2-yl)-2-nitrobenzamide (500 mg, 1.31 mmol, 1.00 equiv) in N,N-dimethylformamide (5 mL), and piperidine (330 mg, 3.88 mmol, 3.00 equiv). The resulting solution was stirred for 4 h at 85° C. in an oil bath. The reaction was then quenched with 100 mL of water. The resulting solution was extracted with 2×100 mL of ethyl acetate and the organic layers combined. The resulting mixture was washed with 2×100 mL of brine. The mixture was dried over sodium sulfate and concentrated under vacuum to give 550 mg (98%) of product as a yellow solid.

Workup

customInto a 50-mL round-bottom flask, was placed
customThe reaction was then quenched with 100 mL of water
extractionThe resulting solution was extracted with 2×100 mL of ethyl acetate
washThe resulting mixture was washed with 2×100 mL of brine
dry with materialThe mixture was dried over sodium sulfate
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-fbd468b6d3834f778bddcf26314a6305
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08809339B2

Reaction notes

Loading…