Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | Methyl 4-(bromomethyl)benzoate | HCID 256687 | — |
| Reactant | HCID 66751033 | HCID 66751033 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 66792734 | HCID 66792734 | 86.1% |
Reaction Steps
A suspension of 4-{2-[4-(2-tert-butylphenyl)piperazin-1-yl]-2-oxoethyl}piperidine-2,6-dione (Example 14, 0.500 g, 1.35 mmol), methyl 4-(bromomethyl)benzoate (0.370 g, 1.62 mmol), and potassium carbonate (0.56 g, 4.05 mmol) in DMF (6 mL) was stirred at room temperature for 16 h. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with saturated sodium hydrogen carbonate solution 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=90:10 to 20:80) to provide methyl 4-[(4-{2-[4-(2-tert-butylphenyl)piperazin-1-yl]-2-oxoethyl}-2,6-dioxopiperidin-1-yl)methyl]benzoate (0.604 g, 86%) as a white amorphous.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08853215B2 |
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| Source dataset | uspto-grants-2014_10 |
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| ORD ID | ord-21e6ca820db44bb8b094d011363ceac4 |
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| Source note | uspto-grants-2014_10 |
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