Sodium Iodide → HCID 17812242, compound

To a suspended solution of 4-(3-indolyl)piperidine (1.0 g, 5.0 mmol) and a 96% 3-dimethylaminopropyl chloride hydrochloride (0.91 g, 5.5 mmol) in acetonitrile (50 mL) was added potassium carbonate (2.07 g, 15 mmol) and sodium iodide (0.82 g, 5.5 mmol), and the resulting mixture was refluxed for 5 hours. After the precipitated salt was filtered off, the filtrate was concentrated, and water (40 mL) was added to the filtrate and the mixture was extracted with chloroform. After drying over anhydrous sodium sulfate, the chloroform layer was concentrated, and the resulting crude product was purified by column chromatography on a silica gel (silica gel NH-DM 1020 produced by Fuji Silysia Chemical Ltd., eluent; ethyl acetate) to afford a free form (1.2 g) of the title compound as pale red crystals. After adding hydrochloric acid/methanol to a solution of the free form in methanol, the mixture was concentrated and was then recrystallized from methanol/ether to afford the title compound (1.2 g, yield: 69%) as pale yellow crystals.

1. temperaturethe resulting mixture was refluxed for 5 hours
2. filtrationAfter the precipitated salt was filtered off
3. concentrationthe filtrate was concentrated
4. additionwater (40 mL) was added to the filtrate
5. extractionthe mixture was extracted with chloroform
6. dry with materialAfter drying over anhydrous sodium sulfate
7. concentrationthe chloroform layer was concentrated
8. customthe resulting crude product was purified by column chromatography on a silica gel (silica gel NH-DM 1020 produced by Fuji Silysia Chemical Ltd., eluent; ethyl acetate)

ORD record

ord-3ef0f8c555544a808891fabc064595fd

Source dataset

uspto-grants-2003_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06642228B1