Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 4-Amino-1-Boc-piperidine | HCID 1268291 | — |
| Reactant | 1-Fluoro-5-methyl-2-nitro-4-(trifluoromethyl)benzene | HCID 59850182 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 59850131 | HCID 59850131 | — |
Reaction Steps
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.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08288412B2 |
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| Source dataset | uspto-grants-2012_10 |
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| ORD ID | ord-fa7c88752b9e4c4099cd185f2231bfff |
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| Source note | uspto-grants-2012_10 |
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