HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → HCID 21921950, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 5-Chloro-2-fluorobenzonitrile | HCID 93653 | — |
| Reactant | 3,5-Dimethylpiperidine | HCID 118259 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 21921950 | HCID 21921950 | 102.8% |
Reaction Steps
To a solution of 5-chloro-2-fluoro-benzonitrile (0.700 g, 4.499 mmol) in anhydrous DMF (8.0 mL) was added 3,5-dimethylpiperdine (0.713 g, 6.299 mmol) and cesium carbonate (4.30 g, 13.497 mmol). The reaction mixture was heated at 80 C for 2 h. Upon cooling to rt, water and ethylacetate was added. The organic layer was separated and the aqueous layer was extracted twice with ethyl acetate. To the combined organic layer was added ether and the organic layer was washed with water and brine, dried (Na2SO4) and concentrated under reduced pressure to give 1.15 g (96%) of 5-chloro-2-(3,5-dimethyl-piperidin-1-yl)-benzonitrile as solid. LCMS 249(M+1)+. The compound was >98% purity and was hence used directly for the next step
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07122580B2 |
| Source dataset | uspto-grants-2006_10 |
| ORD ID | ord-8010d58324834f60ae0b810feb16b418 |
| Source note | uspto-grants-2006_10 |