反应详情

A mixture of 4-cyano-2-(dimethylamino)methylpyridine (800 mg, 4.97 mmol), palladium (80 mg, 10% Pd/C) and concentrated hydrochloric acid (3 mL) in methanol (30 mL) was shaken under 60 psi of hydrogen overnight. The reaction mixture was filtered through diatomaceous earth and the filter cake rinsed with water and methanol. The filtrate was concentrated under reduced pressure and the residue partitioned between water and methylene chloride. The aqueous layer was made alkaline with 1 N sodium hydroxide and extracted with methylene chloride. The organic layer was washed with saturated sodium chloride, dried (sodium sulfate), filtered, and concentrated under reduced pressure to give an orange oil. Purification by flash column chromatography (97:3 2-propanol/ammonium hydroxide) gave 4-aminomethyl-2-(dimethylamino) methylpyridine 37 (492 mg): 1H NMR (500 Hz, CDCl3) δ 8.50 (d, J=5.1 Hz, 1H), 7.37 (s, 1H), 7.15 (d, J=5.1 Hz, 1H), 3.91 (s, 2H), 3.58 (s, 2H), 2.30 (s, 6H); ESI MS m/z 166 [M+H]+.

1. filtrationThe reaction mixture was filtered through diatomaceous earth
2. washthe filter cake rinsed with water and methanol
3. concentrationThe filtrate was concentrated under reduced pressure
4. customthe residue partitioned between water and methylene chloride
5. extractionextracted with methylene chloride
6. washThe organic layer was washed with saturated sodium chloride
7. dry with materialdried (sodium sulfate)
8. filtrationfiltered
9. concentrationconcentrated under reduced pressure
10. customto give an orange oil
11. customPurification by flash column chromatography (97:3 2-propanol/ammonium hydroxide)