Piperidine → HCID 23518812, compound

A mixture of 4-[3-aminobenzoyl]-1-methylpiperidine (25 mg, 0.115 mmol) and (piperidinomethyl)-polystyrene (100 mg, 0.260 mmol) in tetrahydrofuran (2 mL) was allowed to stand for 10 min. 2,3,4,5-Tetrafluorobenzoyl chloride (31 μL, 0.229 mmol) was added to the reaction mixture. The reaction mixture was mixed for 24 h at ambient temperature. The reaction mixture was filtered and the filter cake was rinsed with 7M ammonia in methanol. Glacial acetic acid (0.5 mL) was added to the filtrate solution and the solution was mixed. This mixture was poured over a Varian Mega Bond Elut™ strong cation exchange column. This purification was unsuccessful. The solvent was concentrated in vacuo. The residue was dissolved in water, basified with ammonium hydroxide, and extracted with methylene chloride. The organic extracts were washed with brine, glacial acetic acid (0.5 mL) was added to the organic extracts and the solution was mixed for 5 min. This mixture was poured over a Varian Mega Bond Elut™ strong cation exchange column. The column was rinsed with methanol to remove impurities, then treated with a 7M ammonia in methanol to elute the product from the column. The solvent was evaporated to give 43.7 mg (97%) of the title compound.

1. additionThe reaction mixture was mixed for 24 h at ambient temperature
2. filtrationThe reaction mixture was filtered
3. washthe filter cake was rinsed with 7M ammonia in methanol
4. additionGlacial acetic acid (0.5 mL) was added to the filtrate solution
5. additionthe solution was mixed
6. additionThis mixture was poured over a Varian Mega Bond Elut™ strong cation exchange column
7. customThis purification
8. concentrationThe solvent was concentrated in vacuo
9. dissolutionThe residue was dissolved in water
10. extractionextracted with methylene chloride
11. washThe organic extracts were washed with brine, glacial acetic acid (0.5 mL)
12. additionwas added to the organic extracts
13. additionthe solution was mixed for 5 min
14. additionThis mixture was poured over a Varian Mega Bond Elut™ strong cation exchange column
15. washThe column was rinsed with methanol
16. customto remove impurities
17. additiontreated with a 7M ammonia in methanol
18. washto elute the product from the column
19. customThe solvent was evaporated

ORD record

ord-c83a3be2d0a24f429a9194d2bdefc0ca

Source dataset

uspto-grants-2004_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06777428B1