Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Ethanimidic acid, ethyl ester, hydrochloride (1:1) | HCID 2724290 | — |
| Reactant | tert-Butyl 4-(hydrazinecarbonyl)piperidine-1-carboxylate | HCID 22713165 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 178433970 | HCID 178433970 | 10.5% |
Reaction Steps
4-Hydrazinocarbonyl-piperidine-1-carboxylic acid tert-butyl ester (1.19 g, 5 mmol) was mixed with ethylacetimidate hydrochloride (0.91 g, 7 mmol) in DMF (5 ml) and Et3N (2 ml, 15 mmol) was added. The reaction was stirred for 1 h after which time the DMF was evaporated, the residue redissolved in AcOH and 0.5 g of ammonium acetate added and the reaction heated to 100° C. for a further 3 h. The reaction was then concentrated, redissolved in CH2Cl2, washed with NaHCO3, dried (Na2SO4) and concentrated. The residue was purified by flash column chromatography (CH2Cl2:MeOH 1:0-9:1) to afford the title product (0.14 g, 10%) as a colourless gum. MS: 267.4 (MH+)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07632829B2 |
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| Source dataset | uspto-grants-2009_12 |
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| ORD ID | ord-f72a68f57a1d4ffb8f6635c9348bfa5a |
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| Source note | uspto-grants-2009_12 |
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