Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Citric Acid | HCID 311 | — |
| Reactant | Iodoethane | HCID 6340 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | HCID 86626521 | HCID 86626521 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 86626522 | HCID 86626522 | — |
Reaction Steps
Ethyl [4-(tert-butoxycarbonylamino-methyl)-piperidin-1-yl]-acetate (1.86 g) is dissolved in N,N-dimethylformamide (10 ml), and thereto are added sodium hydride (63%) (1.19 g) and ethyl iodide (6.0 ml), and the mixture is stirred at room temperature for 2 hours. The reaction mixture is made weak basic with a 10% aqueous citric acid solution and a saturated aqueous sodium bicarbonate solution, and extracted with ethyl acetate, and the organic layer is washed with a saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue is purified by silica gel column chromatography (hexane:ethyl acetate=2:1) to give ethyl {4-[(tert-butoxycarbonyl-ethyl-amino)-methyl]-piperidine-1-yl}-acetate (905 mg). MS (m/z): 329 [M+H]+
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07906517B2 |
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| Source dataset | uspto-grants-2011_03 |
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| ORD ID | ord-905ed235d4c54992a3d86d76743840cc |
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| Source note | uspto-grants-2011_03 |
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