Water → HCID 66792768, compound

HRID 534927Notes

Reaction equation

Cl.Cl.[Br:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[C:6]([C:16]([CH3:19])([CH3:18])[CH3:17])[CH:5]=1.C(N(CC)CC)C.Cl[C:28](=[O:34])[C:29]([O:31][CH2:32][CH3:33])=[O:30].O>C1COCC1>[Br:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][N:13]([C:28](=[O:34])[C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH2:12][CH2:11]2)=[C:6]([C:16]([CH3:19])([CH3:18])[CH3:17])[CH:5]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred suspension of 1-(4-bromo-2-tert-butylphenyl)piperazine dihydrochloride (Reference Example 9, 0.300 g, 0.81 mmol) and triethylamine (564 μl, 4.05 mmol) in THF (10 mL) stirring at 0° C. was added ethyl chloro(oxo)acetate (0.144 mg, 1.05 mmol). The mixture was warmed to room temperature. After 16 h the reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with saturated sodium hydrogen carbonate and brine, dried over MgSO4, and the solvent was evaporated under reduced pressure to give the crude product. The product was purified by flash column chromatography (silica gel, n-hexane/ethyl acetate=80:20 to 50:50) to provide ethyl [4-(4-bromo-2-tert-butylphenyl)piperazin-1-yl](oxo)acetate (0.328 g, quant) as a white solid.

Workup

temperatureThe mixture was warmed to room temperature
extractionextracted with ethyl acetate
washThe organic layer was washed with saturated sodium hydrogen carbonate and brine
dry with materialdried over MgSO4
customthe solvent was evaporated under reduced pressure
customto give the crude product
customThe product was purified by flash column chromatography (silica gel, n-hexane/ethyl acetate=80:20 to 50:50)

Sources & evidence

ORD record: ord-2aeb63cc3af0463696a1d2a24f5895dc
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08853215B2

Reaction notes

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