Dichloromethane → HCID 21904839, compound

Temperature

0 °C

The compound from Example 15 (1 g, 2.13 mmol) was dissolved in methylene chloride (2.3 mL) and cooled to 0° C. Trifluoromethane sulfonic acid (1.32 mL, 14.9 mmol) was added slowly to the solution followed by anisole (0.695 mL, 6.39 mmol). The reaction mixture was then stirred at 0° C. for 10 minutes, and then stirred at room temperature for 1 hour, at which point the reaction was complete. The pH of the reaction mixture was then adjusted with 1N NaOH until the pH was basic. The reaction mixture was then transferred to a separatory funnel and extracted with methylene chloride (3×). The combined organic extracts were dried with magnesium sulfate, filtered and concentrated to give a yellow oil. Further purification (2-4% ammonia in 2M solution in methanol/Ethyl acetate) yielded 0.630 g of the desired free amine product (88%). The free amine product (1.85 mmol) was then dissolved in diethyl ether and isopropanol. HCl in 2M solution of diethyl ether (1.85 mmol) was added. The solution was stirred for 30 minutes and a yellow solid was filtered off.

1. stirringstirred at room temperature for 1 hour, at which
2. customThe reaction mixture was then transferred to a separatory funnel
3. extractionextracted with methylene chloride (3×)
4. dry with materialThe combined organic extracts were dried with magnesium sulfate
5. filtrationfiltered
6. concentrationconcentrated
7. customto give a yellow oil
8. customFurther purification (2-4% ammonia in 2M solution in methanol/Ethyl acetate)

ORD record

ord-db010cd5ded945248ddd2fccd707265e

Source dataset

uspto-grants-2010_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07687620B2