HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Trifluoroacetic acid → (4-Aminophenyl)(4-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)benzyl)piperazin-1-yl)methanone
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|---|---|---|
| Edukt | Trifluoroacetic acid | HCID 6422 | — |
| Edukt | Potassium Carbonate | HCID 11430 | — |
| Edukt | Tert-butyl 4-(4-aminobenzoyl)piperazine-1-carboxylate | HCID 2763355 | — |
| Edukt | 2-[4-(Bromomethyl)phenyl]-1,1,1,3,3,3-hexafluoropropan-2-ol | HCID 23527396 | — |
| Lösungsmittel | Acetonitrile | HCID 6342 | — |
| Lösungsmittel | Dichloromethane | HCID 6344 | — |
| Produkt | (4-Aminophenyl)(4-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)benzyl)piperazin-1-yl)methanone | HCID 86638547 | 54,4% |
Reaktionsschritte
tert-Butyl 4-(4-aminobenzoyl)piperazine-1-carboxylate (4.98 mmol, 1.520 g) was dissolved in dichloromethane and trifluoroacetic acid added. The reaction was left overnight and then treated to SCX purification. The intermediate amine was combined with 2-(4-(bromomethyl)phenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol (4.98 mmol, 1.678 g) and potassium carbonate (4.98 mmol, 0.688 g) in acetonitrile (30 mL) and stirred overnight. The reaction was concentrated under reduced pressure and the residue partitioned between water and ethyl acetate. The organic layer was separated and concentrated under reduced pressure. Purification by SCX column chromatography and silica chromatography (eluting with ethyl acetate) gave the title compound (1.25 g).
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US08357679B2 |
| Quelldatensatz | uspto-grants-2013_01 |
| ORD ID | ord-f6ddc34564ef4f779d2af23656d5d23d |
| Quellennotiz | uspto-grants-2013_01 |