Sulfuric Acid → HCID 86652333, compound

To a solution of 3-(ethoxycarbonyl)-1,1-dimethylpiperidinium iodide (5) (2.2 g, 6.9 mmol) in water (45 mL) was added conc. H2SO4 (1.0 mL). Dowex® (1×8, 200-400 mesh ‘Cl’) (2.0 g) was added to this solution. The resulting mixture was heated to reflux for 18 h. The resin was filtered off and the aqueous solution was concentrated. The resultant brown oil was triturated with isopropanol to form an off-white precipitate. The precipitate was washed with isopropanol until the color became white. The resulting white precipitate was dried under reduced pressure to give 1.0 g, 93% yield of the desired product. Positive mode ESI/MS: m/z=158 (M+H); confirmed by 1H NMR.

1. additionDowex® (1×8, 200-400 mesh ‘Cl’) (2.0 g) was added to this solution
2. temperatureThe resulting mixture was heated
3. temperatureto reflux for 18 h
4. filtrationThe resin was filtered off
5. concentrationthe aqueous solution was concentrated
6. customThe resultant brown oil was triturated with isopropanol
7. customto form an off-white precipitate
8. washThe precipitate was washed with isopropanol until the color
9. customThe resulting white precipitate was dried under reduced pressure

ORD record

ord-bbc3e194579e4800abf1080b0cb37bf6

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08519125B2