Water → tert-Butyl 4-(4-nitroanilino)piperidine-1-carboxylate

HRID 1791908Notes

Reaction equation

NN1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.F[C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=1.[CH:25]([N:28](CC)C(C)C)(C)C.O>CN1CCCC1=O>[C:11]([O:10][C:8]([N:5]1[CH2:4][CH2:3][CH:25]([NH:28][C:16]2[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=2)[CH2:7][CH2:6]1)=[O:9])([CH3:12])([CH3:13])[CH3:14]

Participants

Conditions

Temperature: 80 °C

Procedure

4-Amino-1-tert-butoxycarbonylpiperazine (3.00 g), 4-fluoronitrobenzene (2.54 g) and N,N-diisopropylethylamine (8.82 g) were dissolved in N-methyl-2-pyrrolidone (30 mL), and the mixture was stirred at 80° C. for 18 hr. The reaction mixture was added to water and the mixture was extracted with ethyl acetate. The extract was washed with brine and dried. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to give 1-tert-butoxycarbonyl-4-(4-nitrophenyl)aminopiperidine (2.55 g) as a white solid.

Workup

extractionthe mixture was extracted with ethyl acetate
washThe extract was washed with brine
customdried
customThe solvent was evaporated under reduced pressure
customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-cdc8330fdabf4b8090f409cf85b62274
Source dataset: uspto-grants-2006_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07074794B2

Reaction notes

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