Hydrochloric Acid → HCID 18794800, compound

A mixture of 2-methoxy-3-[4-[2-[N-methyl-N-(2-pyridyl)amino]ethoxyl]-phenyl]propanonitrile (1.15 g), sodium hydroxide solution (10% w/v; 10 mL) and methanol (20 mL) was heated at reflux for 2.5 hrs, cooled and neutralised to pH7 with dilute HCl. The mixture was evaporated in vacuo and the residue redissolved in methanol presaturated with hydrogen chloride gas. The mixture was allowed to stand at room temperature for 7 days, then evaporated. Saturated sodium bicarbonate solution (100 mL) was added and the suspension extracted with ethyl acetate (3×200 mL). The combined ethyl acetate solutions were washed with water (2×500 mL) and brine (500 mL), dried (MgSO4) and evaporated. The resulting gum was chromatographed on silica gel with 1% methanol in dichloromethane to afford the title compound, a gum.

1. temperaturewas heated
2. temperatureat reflux for 2.5 hrs
3. customThe mixture was evaporated in vacuo
4. dissolutionthe residue redissolved in methanol
5. customevaporated
6. additionSaturated sodium bicarbonate solution (100 mL) was added
7. extractionthe suspension extracted with ethyl acetate (3×200 mL)
8. washThe combined ethyl acetate solutions were washed with water (2×500 mL) and brine (500 mL)
9. dry with materialdried (MgSO4)
10. customevaporated
11. customThe resulting gum was chromatographed on silica gel with 1% methanol in dichloromethane

ORD record

ord-1f030b2df2db4f2b8210c1a8eb7bf4ec

Source dataset

uspto-grants-1999_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05869495