Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Diethylene Glycol | HCID 8117 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | (3S)-(+)-1-Benzyl-3-aminopyrrolidine | HCID 1519353 | — |
| Reactant | 2-Chloro-6-methyl-4-(trifluoromethyl)pyridine | HCID 2736626 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 57970191 | HCID 57970191 | 24.4% |
Reaction Steps
A mixture of 2-chloro-6-methyl-4-trifluoromethylpyridine (0.196 g), (S)-1-benzyl-3-aminopyrrolidine (0.529 g), diethylene glycol (4 mL), and N,N-diisopropylethylamine (0.52 mL) was heated at 140° C. for 2 h using a microwave reaction apparatus. After completion of the reaction, water and ethyl acetate were added to the reaction solution, the mixture was extracted with ethyl acetate, washed with saturated brine, and then dried with anhydrous magnesium sulfate, then the desiccant was removed by filtration, and then the crude product obtained by concentration under reduced pressure was purified by silica gel column chromatography (silica gel, hexane/ethyl acetate=5:1-2:1) to obtain (S)-N-(1-benzylpyrrolidin-3-yl)-6-methyl-4-trifluoromethylpyridin-2-amine (0.082 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08044068B2 |
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| Source dataset | uspto-grants-2011_10 |
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| ORD ID | ord-df0dc02cf1a34c1096c54260fd9d2e96 |
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| Source note | uspto-grants-2011_10 |
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