Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Phenethyl bromide | HCID 7666 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | Ethyl 4-piperidinecarboxylate | HCID 70770 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 10106733 | HCID 10106733 | 84% |
Reaction Steps
A mixture of ethyl isonipecotate (64 mmol; 10.0 g), anhydrous potassium carbonate (192 mmol; 26.5 g) and phenylethyl bromide (77 mmol, 14.25 g) in anhydrous N,N-dimethylformamide (100 ml) was stirred at 70° C. for 5 hours 30 minutes. After cooling, the reaction mixture was diluted with water (300 ml) and extracted with ethyl acetate (3×200 ml). The combined organic phases were washed with saturated NaCl solution (3×100 ml), dried over sodium sulfate and evaporated under reduced pressure. A crude product was obtained, which was purified on a column of alumina (eluting with 2/1 n-hexane/ethyl acetate) to give 14.0 g (84%) of pure product as a yellow oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08686147B2 |
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| Source dataset | uspto-grants-2014_04 |
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| ORD ID | ord-15f468eacc54423f82343dd6eb827709 |
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| Source note | uspto-grants-2014_04 |
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