Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Allyl bromide | HCID 7841 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | HCID 70873837 | HCID 70873837 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 86719552 | HCID 86719552 | 39% |
Reaction Steps
To a stirred solution of tert-butyl 4-((5-chloro-3-(methoxycarbonyl)-2-methylphenyl)amino)piperidine-1-carboxylate (0.70 g, 1.82 mmol) in DMF (7 mL), was added NaH (0.052 g, 2.19 mmol) at 0° C. After stirring for 20 minutes, 3-bromoprop-1-ene (0.44 g, 3.64 mmol) was added and the mixture was heated at 80° C. for 15 h. On completion, the reaction mass was quenched with ice cold water and extraction was carried out using DCM. The combined organic layers were dried, concentrated under reduced pressure and the residue was purified by column chromatography to afford the title compound (0.3 g, 39%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09376422B2 |
|---|
| Source dataset | uspto-grants-2016_06 |
|---|
| ORD ID | ord-2de09686e4d34f1398429d9f86aeabb8 |
|---|
| Source note | uspto-grants-2016_06 |
|---|