HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ethyl isocyanate → 2-((2-cyano-3-nitrophenoxy)methyl)-N-ethylpiperidine-1-carboxamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ethyl isocyanate | HCID 8022 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 2-Nitro-6-(piperidin-2-ylmethoxy)benzonitrile hydrochloride | HCID 86714298 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 2-((2-cyano-3-nitrophenoxy)methyl)-N-ethylpiperidine-1-carboxamide | HCID 86714297 | 87% |
Reaction Steps
To a solution of 2-nitro-6-(piperidin-2-ylmethoxy)benzonitrile hydrochloride (Example 26d, 0.5 g, 1.68 mmol) in THF were added triethylamine (0.514 mL, 3.7 mmol) and ethylisocyanate (0.2 mL, 2.52 mmol) and the reaction mixture was stirred at room temperature under nitrogen for 3 hours. The solution was then diluted with water and extracted with EtOAc, the combined organic phases were washed with brine, dried over MgSO4, filtered and evaporated to give 2-((2-cyano-3-nitrophenoxy)methyl)-N-ethylpiperidine-1-carboxamide (0.485 g, 87%) which was used in the next step without further purification. MS 333 (MH+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09420814B2 |
| Source dataset | uspto-grants-2016_08 |
| ORD ID | ord-620a24eca2644401ab90b5cbf7130053 |
| Source note | uspto-grants-2016_08 |