Triphenylphosphine → 2-[(Piperidin-4-yl)oxy]benzonitrile

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]+

1. concentrationThe reaction mixture was then concentrated in vacuo
2. stirringThe reaction mixture was stirred at room temperature for 18 hours
3. concentrationwas then concentrated in vacuo
4. customThe residue was partitioned between water and ethyl acetate
5. customthe aqueous layer was separated
6. washwashed with ethyl acetate (2×100 mL)
7. extractionextracted with diethyl ether (3×100 mL)
8. dry with materialThe combined organic solution was dried over magnesium sulfate
9. concentrationconcentrated in vacuo

ORD record

ord-1fcd5453d5ba4517b63a6c030a1bacd7

Source dataset

uspto-grants-2009_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07557131B2