반응 #312999

반응 방정식

1-Boc-4-hydroxypiperidine

2-cyanophenol

triphenylphosphine

di-tert-butyl azodicarboxylate

→

title compound

2-(Piperidin-4-yloxy)benzonitrile

용매

tetrahydrofuran

반응 조건

후처리

1. 1
   농축The reaction mixture was then concentrated in vacuo
2. 2
   workup.STIRRINGThe reaction mixture was stirred at room temperature for 18 hours
3. 3
   농축was then concentrated in vacuo
4. 4
   기타The residue was partitioned between water and ethyl acetate
5. 5
   기타the aqueous layer was separated
6. 6
   세척washed with ethyl acetate (2×100 mL)
7. 7
   추출extracted with diethyl ether (3×100 mL)
8. 8
   건조The combined organic solution was dried over magnesium sulfate
9. 9
   농축concentrated in vacuo

실험 절차

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]+

출처