Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 2-Chloronicotinonitrile | HCID 81079 | — |
| Reactant | HCID 23023142 | HCID 23023142 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Product | HCID 67413381 | HCID 67413381 | 58.1% |
Reaction Steps
To a solution of 4-(3-hydroxy-benzyl)-piperazine-1-carboxylic acid tert-butyl ester (300 mg, 1.0 mmol) in DMSO (5.0 mL) were added Cs2CO3 (660 mg, 2.0 mmol) and 2-chloro-3-pyridinecarbonitrile (172 mg, 1.2 mmol). The mixture was heated at 60° C. for 90 min. The reaction mixture was cooled to rt, poured into water, and extracted with EtOAc (3×). The organic layer was separated and dried (Na2SO4). The crude residue was purified (FCC) to give 4-[3-(3-cyano-pyridin-2-yloxy)-benzyl]-piperazine-1-carboxylic acid tert-butyl ester (229 mg, 56%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08877769B2 |
|---|
| Source dataset | uspto-grants-2014_11 |
|---|
| ORD ID | ord-30c3a8a36aaa4becba4191e245c3d9c0 |
|---|
| Source note | uspto-grants-2014_11 |
|---|