Reaktion #309516

Reaktionsgleichung

1-Boc-4-hydroxypiperidine

2-cyanophenol

triphenylphosphine

di-tert-butyl azodicarboxylate

→

title compound

2-(Piperidin-4-yloxy)benzonitrile

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenThe reaction mixture was then concentrated in vacuo
2. 2
   workup.STIRRINGThe reaction mixture was stirred at room temperature for 18 hours
3. 3
   Einengenwas then concentrated in vacuo
4. 4
   SonstigeThe residue was partitioned between water and ethyl acetate
5. 5
   Sonstigethe aqueous layer was separated
6. 6
   Waschenwashed with ethyl acetate (2×100 mL)
7. 7
   Extraktionextracted with diethyl ether (3×100 mL)
8. 8
   TrocknenThe combined organic solution was dried over magnesium sulfate
9. 9
   Einengenconcentrated in vacuo

Vorschrift

1-Boc-4-hydroxypiperidine (20 g, 99.35 mmol) and 2-cyanophenol (11.82 g, 99.35 mmol) were added to mixture of triphenylphosphine (26.06 g, 99.35 mmol) and di-tert-butyl azodicarboxylate (19.56 mL, 99.35 mmol) in tetrahydrofuran (800 mL) and the mixture was stirred at room temperature for 18 hours. The reaction mixture was then concentrated in vacuo and the residue was taken up in hydrochloric acid (4M in dioxane, 300 mL). The reaction mixture was stirred at room temperature for 18 hours and was then concentrated in vacuo. The residue was partitioned between water and ethyl acetate and the aqueous layer was separated and washed with ethyl acetate (2×100 mL). The aqueous solution was then basified with 2M sodium hydroxide solution and then extracted with diethyl ether (3×100 mL). The combined organic solution was dried over magnesium sulfate and concentrated in vacuo to afford the title compound as a white solid in quantitative yield. LRMS ESI m/z 203 [M+H]+

Quelle