Hydrochloric Acid → HCID 11045506, compound

1-(3,4-Dimethoxyphenyl)-2,3,4,9-tetrahydro-1H-β-carboline (1.854 g, 6.04 mmol) (prepared as in Example 11) and KOt-Bu (1.14 g, 10.15 mmol) were stirred in DMF (60 mL) at room temperature for 10 min. Oxygen was bubbled through the solution for 1 h. The reaction mixture was neutralized with 1N HCl solution (10.15 mL, 10.15 mmol) and the water removed in vacuo as an azeotrope with toluene. Silica gel (˜5 g) was added to the residual DMF solution, followed by diethyl ether (600 mL), which resulted in precipitation of the product onto the silica gel. The diethyl ether was decanted and the silica gel was washed with diethyl ether (2×100 mL). After the solvent was decanted and any remaining trace amounts evaporated, the residue was purified by column chromatograph (silica gel; EtOH:EtOAc=1:9) to yield the product as a bright yellow solid. The product was recrystallized from methanol.

1. customOxygen was bubbled through the solution for 1 h
2. customthe water removed in vacuo as an azeotrope with toluene
3. additionSilica gel (˜5 g) was added to the residual DMF solution
4. customresulted in precipitation of the product onto the silica gel
5. customThe diethyl ether was decanted
6. washthe silica gel was washed with diethyl ether (2×100 mL)
7. customAfter the solvent was decanted
8. customany remaining trace amounts evaporated
9. customthe residue was purified by column chromatograph (silica gel; EtOH:EtOAc=1:9)

ORD record

ord-9eaad77115ce4c4a8c5c361be4ab0a3e

Source dataset

uspto-grants-2003_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06635638B2