Dichloromethane → HCID 131727774, compound

The [3-fluoro-4-(3-methoxy-phenoxy)-benzyl]-(3-methyl-butyl)-amine (460 mg, 1.45 mmol) was dissolved in dichloromethane (10 ml) and cooled to −78° C. as boron tribromide (7.25 mL of a 1.0 M in dichloromethane, 7.25 mmol) was added slowly. After 1 hour at −78° C., the reaction was allowed to warm to room temperature. After 4 hours at room temperature the reaction mixture was carefully being quenched with cold water before the pH was adjusted to 10.0 using concentrated ammonium hydroxide. The reaction mixture was extracted with dichloromethane two times and the combined organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated. The residue was purified by preparative thin layer chromatography on silica eluting with 5% methanol in ethyl acetate. The HCl salt of the product thus isolated was formed by dissolving the free base in ethyl acetate and adding 1 ml of 4.0 M HCl in dioxane and evaporating to afford the product (2A) a solid.

1. addition7.25 mmol) was added slowly
2. customAfter 4 hours at room temperature the reaction mixture was carefully being quenched with cold water before the pH
3. extractionThe reaction mixture was extracted with dichloromethane two times
4. washthe combined organic layers were washed with brine
5. dry with materialdried over sodium sulfate
6. filtrationfiltered
7. concentrationconcentrated
8. customThe residue was purified by preparative thin layer chromatography on silica eluting with 5% methanol in ethyl acetate

ORD record

ord-067eec96e98f4d429dc90d5405691528

Source dataset

uspto-grants-2009_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07618996B2