Pyridine → 4-(Pyridin-3-yl)butanenitrile

To a solution of 0.66 mL (5.11 mmol) 3-pyridine propanol in 5 mL CH2Cl2 at 0° C. was added 0.62 mL (7.67 mmol) pyridine and 0.47 mL (6.14 mmol) methanesulfonyl chloride and the reaction stirred for 4 h. The solution was concentrated under reduced pressure and the crude mesylate dissolved in 10 mL DMF. To this solution was added 902 mg (18.41 mmol) sodium cyanide and the reaction stirred at 60° C. for 3 days. Then the solution was cooled, diluted with H2O (30 mL) and extracted with EtOAc (3×20 mL). The combined organic layers were washed with H2O, dried over MgSO4, and the solvent removed under reduced pressure to give a dark red oil. The crude nitrile was purified by dissolving in EtOAc, washing with H2O, concentrating, and filtering through a silica gel plug (5% MeOH in CH2Cl2) to yield 425 mg (57%) of the nitrile.

1. concentrationThe solution was concentrated under reduced pressure
2. dissolutionthe crude mesylate dissolved in 10 mL DMF
3. stirringthe reaction stirred at 60° C. for 3 days
4. temperatureThen the solution was cooled
5. extractionextracted with EtOAc (3×20 mL)
6. washThe combined organic layers were washed with H2O
7. dry with materialdried over MgSO4
8. customthe solvent removed under reduced pressure
9. customto give a dark red oil
10. customThe crude nitrile was purified
11. dissolutionby dissolving in EtOAc
12. washwashing with H2O
13. concentrationconcentrating
14. filtrationfiltering through a silica gel plug (5% MeOH in CH2Cl2)

ORD record

ord-234b2179a6334cf18d90365368c11afd

Source dataset

uspto-grants-2003_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06518285B2