Triethylamine → HCID 85869821, compound

To a ice-bath cooled solution of 3-(2-hydroxyethyl)isoquinoline (Description 111; 4.85 g, 28 mmol) and triethylamine (5.07 ml, 36.4 mmol) in anhydrous dichloromethane (100 ml) was added slowly methanesulfonyl chloride (2.49 ml, 32.2 mmol), and the resulting mixture stirred at room temperature for 1 hour. The mixture was washed with water (200 ml), sat NaCl (100 ml), dried over Na2SO4, filtered and evaporated. The residue was dissolved in anhydrous N,N-dimethylformamide (100 ml) and sodium azide (2.00 g, 30.8 mmol) added and the resulting mixture stirred at room temperature for 4 days. The mixture was poured into water (400 ml), and extracted with EtOAc (3×100 ml). The combined EtOAc layers were washed with water (3×200 ml), saturated aqueous NaCl (100 ml), dried over Na2SO4, filtered and evaporated to give the title compound (5.6 g, 100%).

1. washThe mixture was washed with water (200 ml)
2. dry with materialdried over Na2SO4
3. filtrationfiltered
4. customevaporated
5. dissolutionThe residue was dissolved in anhydrous N,N-dimethylformamide (100 ml)
6. stirringthe resulting mixture stirred at room temperature for 4 days
7. extractionextracted with EtOAc (3×100 ml)
8. washThe combined EtOAc layers were washed with water (3×200 ml), saturated aqueous NaCl (100 ml)
9. dry with materialdried over Na2SO4
10. filtrationfiltered
11. customevaporated

ORD record

ord-059521bf0da3427a9f58ff5db48fdbbe

Source dataset

uspto-grants-2007_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07285563B2