Pyridine → N-(bicyclo[2.2.1]hept-5-en-2-ylmethyl)methanesulfonamide

Temperature

0 °C

Into a dry 500 ml round bottom flask equipped with a magnetic stirrer, condenser and an addition funnel was added 75 ml of dry distilled tetahydrofuran, 32 g (0.41 moles) of pyridine and 50 g (0.41 moles) of norbornyl amine. The reaction mixture was cooled to 0° C. To the mixture was added via the additional funnel 47 g (0.41 moles) of methanesulfonyl chloride and the reaction mixture was stirred overnight. The reaction mixture was filtered to remove the pyridinium hydrochloride salt and the filtrate was rotovaped to remove tetrahydrofuran, resulting in a solid. The solid was dissolved in diethylether, and the resulting solution was extracted several times with deionized water. After treating with decolorizing carbon and drying over anhydrous sodium sulfate, the solution was filtered and the solvent was removed by rotary evaporation. The solid product was recrystallized from toluene and dried under reduced pressure in 76% yield, mp 60-62° C. The product was identified by 1H and 13C NMR and IR spectroscopy.

1. customInto a dry 500 ml round bottom flask equipped with a magnetic stirrer, condenser and an addition funnel
2. additionwas added 75 ml
3. customof dry
4. filtrationThe reaction mixture was filtered
5. customto remove the pyridinium hydrochloride salt
6. customto remove tetrahydrofuran
7. customresulting in a solid
8. extractionthe resulting solution was extracted several times with deionized water
9. additionAfter treating with decolorizing carbon
10. dry with materialdrying over anhydrous sodium sulfate
11. filtrationthe solution was filtered
12. customthe solvent was removed by rotary evaporation
13. customThe solid product was recrystallized from toluene
14. customdried under reduced pressure in 76% yield, mp 60-62° C

ORD record

ord-307678d230874c18b55f5f69414d0a05

Source dataset

uspto-grants-2001_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06235849B1