Water → HCID 59850131, compound

HRID 2064161Notes

Reaction equation

F[C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([C:9]([F:12])([F:11])[F:10])=[CH:4][C:3]=1[N+:13]([O-:15])=[O:14].C(N(C(C)C)CC)(C)C.[NH2:25][CH:26]1[CH2:31][CH2:30][N:29]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:28][CH2:27]1.O>CN(C)C=O>[CH3:8][C:6]1[C:5]([C:9]([F:12])([F:11])[F:10])=[CH:4][C:3]([N+:13]([O-:15])=[O:14])=[C:2]([NH:25][CH:26]2[CH2:27][CH2:28][N:29]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:30][CH2:31]2)[CH:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

1-Fluoro-5-methyl-2-nitro-4-(trifluoromethyl)benzene (D56) (4.9 mmol, 1.1 g) was dissolved in dry dimethylformamide (3 ml) and diisopropylethylamine (1 eq., 4.9 mmol, 0.460 ml), 1,1-dimethylethyl 4-amino-1-piperidinecarboxylate (1 eq., 4.9 mmol, 981 mg) were added at room temperature and the mixture was stirred at 80° C. for 3 hours. The crude mixture was then cooled to room temperature and water was added; the aqueous solution was extracted with ethyl acetate; organics were alternatively washed with brine and water. The organics were combined dried over Na2SO4, filtered and the solvent was evaporated to afford the crude compound that was purified by chromatography (ethyl acetate-n-hexane) to yield the title compound, 1.29 g, 65%, M+−H=402.

Workup

extractionthe aqueous solution was extracted with ethyl acetate
washorganics were alternatively washed with brine and water
dry with materialThe organics were combined dried over Na2SO4
filtrationfiltered
customthe solvent was evaporated
customto afford the crude compound that
customwas purified by chromatography (ethyl acetate-n-hexane)

Sources & evidence

ORD record: ord-fa7c88752b9e4c4099cd185f2231bfff
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08288412B2

Reaction notes

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