Water → 1,1-Dimethylethyl 4-[(5-chloro-4-methyl-2-nitrophenyl)amino]-1-piperidinecarboxylate

HRID 2064124

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6](Cl)[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[CH3:12].C(N(C(C)C)CC)(C)C.[NH2:22][CH:23]1[CH2:28][CH2:27][N:26]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:25][CH2:24]1.O>CN(C)C=O>[Cl:1][C:2]1[C:3]([CH3:12])=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([NH:22][CH:23]2[CH2:24][CH2:25][N:26]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:27][CH2:28]2)[CH:7]=1

Participants

Conditions

Temperature: 100 °C

Procedure

1,5-Dichloro-2-methyl-4-nitrobenzene (2.42 mmol, 500 mg) was dissolved in dry dimethylformamide (5 ml) and diisopropylethylamine (1 eq., 2.42 mmol, 0.413 ml), 1,1-dimethylethyl 4-amino-1-piperidinecarboxylate (1 eq., 2.42 mmol, 484 mg) were added at room temperature and the mixture was stirred at 100° C. overnight. The crude mixture was then cooled to room temperature and water was added; the aqueous solution was extracted with ethyl acetate (3×); 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/hexane) to yield the title compound, 98 mg, 11%, bright orange solid.

Workup

extractionthe aqueous solution was extracted with ethyl acetate (3×)
washorganics were alternatively washed with brine and water
dry with materialdried over Na2SO4
filtrationfiltered
customthe solvent was evaporated
customto afford the crude compound that
customwas purified by chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record: ord-299f2183c10d4f508b68f534b983dc8b
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08288412B2

Linked notes

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