HuagongsheHuagongshe Chemistry Print Report · For research reference only
Picolinic acid → N,N'-Bis(picolinovl)-2.5-diazabicyclo[2 .2.2]octane
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Picolinic acid | HCID 1018 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate | HCID 151348 | — |
| Reactant | 2,5-Diazabicyclo(2.2.2)octane | HCID 423347 | — |
| Reactant | 1-Hydroxybenzotriazole hydrate | HCID 2796029 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Sodium chloride; water | HCID 57417360 | — |
| Product | N,N'-Bis(picolinovl)-2.5-diazabicyclo[2 .2.2]octane | HCID 9905241 | — |
Reaction Steps
Combine 2,5-diazabicyclo[2.2.2]octane (1 molar equivalent), picolinic acid (3 molar equivalents), BOP reagent (3 molar equivalents), HOBt hydrate (3 molar equivalents) and iPr2NEt (5 molar eqiuvalents) in DMF. Maintain the reaction at room temperature for 18 h. Quench the reaction by pouring into brine and extracting with EtOAc. Dry the combined organic extracts over Na2SO4 and remove the solvent in vacuo. Purification by flash chromatography gives the title product.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06200986B1 |
| Source dataset | uspto-grants-2001_03 |
| ORD ID | ord-bc07b0f986774c52b74867c3f8109621 |
| Source note | uspto-grants-2001_03 |