Sodium Hydroxide → HCID 22998557, compound

1 N Sodium hydroxide was added to 2-(N,N-dimethylamino) methyl-7-methoxy-1-tetralone hydrochloride (8.46 g) to convert it into a free compound, which was extracted with ethyl acetate. The extract was dried, and then concentrated. Sodium borohydride (2.32 g) was added to a methanol solution (150 ml) of the resulting residue, with cooling with ice, which was then stirred at room temperature for 12 hours. Water was added to the reaction mixture, which was concentrated under reduced pressure, and then extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, then dried, and concentrated. Concentrated hydrochloric acid (6.4 g) and 10% palladium-carbon (0.7 g) were added to an ethanol solution (100 ml) of the resulting residue, which was thus catalytically reduced under a hydrogen pressure of 5 atmospheres at 60° C. for 8 hours. The catalyst was removed from the reaction mixture through filtration, and the filtrate was concentrated. The residue was recrystallized from methanol-ethyl acetate to obtain the entitled compound (6.53 g).

1. extractionwas extracted with ethyl acetate
2. customThe extract was dried
3. concentrationconcentrated
4. additionSodium borohydride (2.32 g) was added to a methanol solution (150 ml) of the resulting residue
5. temperaturewith cooling with ice, which
6. additionWater was added to the reaction mixture, which
7. concentrationwas concentrated under reduced pressure
8. extractionextracted with ethyl acetate
9. washThe organic layer was washed with a saturated aqueous sodium chloride solution
10. customdried
11. concentrationconcentrated
12. additionConcentrated hydrochloric acid (6.4 g) and 10% palladium-carbon (0.7 g) were added to an ethanol solution (100 ml) of the resulting residue, which
13. customat 60° C.
14. customfor 8 hours
15. customThe catalyst was removed from the reaction mixture through filtration
16. concentrationthe filtrate was concentrated
17. customThe residue was recrystallized from methanol-ethyl acetate

ORD record

ord-c64dc282910a4f9c82dbf8e1e3ed238d

Source dataset

uspto-grants-2003_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06613805B2