Piperidine → HCID 23518818, compound

A mixture of 4-[3-aminobenzoyl]-1-methylpiperidine (25 mg, 0.115 mmol) and (piperidinomethyl)-polystyrene (50 mg, 0.130 mmol) in tetrahydrofuran (1 mL) was allowed to stand for 5 min. 3-fluorobenzoyl chloride (28 μL, 0.229 mmol) and tetrahydrofuran (1 mL) were added to the reaction mixture. The reaction mixture was mixed for 18 h at ambient temperature. The reaction mixture was filtered and the filter cake was rinsed with methanol. Glacial acetic acid (0.5 mL) was added to the filtrate solution and allowed to stand 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 mg (>100%) of the title compound.

1. additionThe reaction mixture was mixed for 18 h at ambient temperature
2. filtrationThe reaction mixture was filtered
3. washthe filter cake was rinsed with methanol
4. additionGlacial acetic acid (0.5 mL) was added to the filtrate solution
5. waitto stand for 5 min
6. additionThis mixture was poured over a Varian Mega Bond Elut™ strong cation exchange column
7. washThe column was rinsed with methanol
8. customto remove impurities
9. additiontreated with a 7M ammonia in methanol
10. washto elute the product from the column
11. customThe solvent was evaporated

ORD record

ord-6e714816ccf843a8ac85a7cdb1fb73ba

Source dataset

uspto-grants-2004_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06777428B1