Piperidine → HCID 86653944, compound

Temperature

50 °C

To the mixture of 6-chloro-7-fluoroindolin-2-one (1.1 g, 5.9 mmol) (Natrochem) and 3-chloro-2-fluorobenzaldehyde (1.4 g, 8.9 mmol) (Aldrich) in methanol (50 mL) was added piperidine (1.5 g, 17.8 mmol) (Aldrich) dropwise. The mixture was then heated at 50° C. for 3 h. After cooled to room temperature, the mixture was concentrated. The residue was partitioned between ethyl acetate and water. The organic layer was separated, and aqueous layer was extracted with ethyl acetate. The organic layers were combined, washed with brine, dried over MgSO4, and concentrated to half its volume. The mixture was filtered and resulting precipitate was collected, dried to give the first batch of desired product (1.4 g). The filtrate was concentrated, and residue was purified by chromatography (20-40% EtOAc in hexanes) to give the second batch of desired product (0.44 g). The two batches were combined to give E/Z-6-chloro-3-(3-chloro-2-fluoro-benzylidene)-7-fluoro-1,3-dihydro-indol-2-one as a yellow solid (Yield 1.84 g, 89%).

1. temperatureAfter cooled to room temperature
2. concentrationthe mixture was concentrated
3. customThe residue was partitioned between ethyl acetate and water
4. customThe organic layer was separated
5. extractionaqueous layer was extracted with ethyl acetate
6. washwashed with brine
7. dry with materialdried over MgSO4
8. concentrationconcentrated to half its volume
9. filtrationThe mixture was filtered
10. customresulting precipitate
11. customwas collected
12. customdried

ORD record

ord-ea2082a368594d648e2d33e8576ed333

Source dataset

uspto-grants-2012_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08217044B2