HCID 53980652, compound → 3-Pyridineethanamine,beta-methyl-(9CI)

To a solution of 2-(3-pyridyl)-1-nitropropane (0.91 g, 5.48 mmol) in 20 mL of ethanol and 0.1 mL of 12N HCl was added 10% Pd/C (1.00 g) under argon. The solution was evacuated and flushed with hydrogen several times, place under an atmosphere of hydrogen and vigorously stirred. After 14 h the mixture was evacuated and flushed with argon several times, filtered through celite and washed with 200 mL of ethanol. The volatiles were removed in vacuo to provide a residue which was partitioned between methylene chloride (100 mL) and NaOH (50 mL, 10%) and the aqueous layer was extracted with methylene chloride (2×100 mL). The combined organic layers were dried over MgSO4, filtered, concentrated in vacuo and the residue was purified by flash column chromatography (20×150 mm column of SiO2, CH2Cl2 /CH2Cl2 saturated with NH3 /MeOH 60:39:1) to give the title compound as an oil:

1. customThe solution was evacuated
2. customflushed with hydrogen several times, place under an atmosphere of hydrogen
3. customAfter 14 h the mixture was evacuated
4. customflushed with argon several times
5. filtrationfiltered through celite
6. washwashed with 200 mL of ethanol
7. customThe volatiles were removed in vacuo
8. customto provide a residue which
9. customwas partitioned between methylene chloride (100 mL) and NaOH (50 mL, 10%)
10. extractionthe aqueous layer was extracted with methylene chloride (2×100 mL)
11. dry with materialThe combined organic layers were dried over MgSO4
12. filtrationfiltered
13. concentrationconcentrated in vacuo
14. customthe residue was purified by flash column chromatography (20×150 mm column of SiO2, CH2Cl2 /CH2Cl2 saturated with NH3 /MeOH 60:39:1)

ORD record

ord-1f6c10c6596a4714aa6a4e5c3df11e7c

Source dataset

uspto-grants-1999_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05866573