Benzylamine → HCID 117839224, compound

To a dichloromethane solution (40 mL) of (E)-1-(3-chloroprop-1-en-1-yl)-4-fluorobenzene (2.40 g, 14.0 mmol), rhodium (II) acetate (57.7 mg, 0.140 mmol) was added and then a dichloromethane solution (20 mL) of ethyl diazoacetate (1.92 g, 16.8 mmol) was added dropwise at room temperature over 18 hours with stirring. After completion of the reaction, the reaction solution was concentrated and N,N-dimethylformamide (20 mL), benzylamine (1.50 g, 14.0 mmol), and sodium bicarbonate (1.18 g, 14.0 mmol) were added to the resultant residue and the resultant mixture was stirred at 150° C. for 2 hours. After completion of the reaction, ethyl acetate was added to the reaction solution and the resultant mixture was washed with 1 M hydrochloric acid and a saturated sodium chloride aqueous solution. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. To the obtained residue, ethyl acetate was added and the resultant mixture was filtered. The filtrate was concentrated under reduced pressure and purified by silica gel column chromatography (hexane/ethyl acetate=3/1) to obtain the title compound (956 mg, yield 24%).

1. customAfter completion of the reaction
2. concentrationthe reaction solution was concentrated
3. additionwas added to the reaction solution
4. washthe resultant mixture was washed with 1 M hydrochloric acid
5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
6. concentrationconcentrated under reduced pressure
7. additionTo the obtained residue, ethyl acetate was added
8. filtrationthe resultant mixture was filtered
9. concentrationThe filtrate was concentrated under reduced pressure
10. custompurified by silica gel column chromatography (hexane/ethyl acetate=3/1)

ORD record

ord-bfb4ff568a5e4c4eb6d655eab232da3a

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09403798B2