Triethylamine → 3-{1-[(3-chloropropyl)sulfonyl]-4-piperidinyl}-5-phenyl-1H-indole-7-carboxamide

Temperature

0 °C

To a solution of 5-phenyl-3-(4-piperidinyl)-1H-indole-7-carboxamide (404 mg, 1.26 mmol) in CH2Cl2 at 0° C., triethylamine (0.7 mL, 5.04 mmol) and 3-chloropropanesulfonyl chloride (0.23 mL, 1.89 mmol) were added. The reaction mixture was stirred at 0° C. for 30 min. The reaction mixture was partitioned between CH2Cl2 (100 mL) and water (50 mL). The organic layer was separated and the aqueous layer was extracted with CH2Cl2 (2×100 mL). The combined organic phase washed with brine (50 mL), dried over magnesium sulfate and filtered. The solvent was removed under reduced pressure and purified via filtration through an SPE Cartridge (Aminopropyl NH2, 500 mg/6 mL) to give the title compound (370 mg, 64%).

1. customThe reaction mixture was partitioned between CH2Cl2 (100 mL) and water (50 mL)
2. customThe organic layer was separated
3. extractionthe aqueous layer was extracted with CH2Cl2 (2×100 mL)
4. washThe combined organic phase washed with brine (50 mL)
5. dry with materialdried over magnesium sulfate
6. filtrationfiltered
7. customThe solvent was removed under reduced pressure
8. filtrationpurified via filtration through an SPE Cartridge (Aminopropyl NH2, 500 mg/6 mL)

ORD record

ord-ddc1d0f50bae4d188d7e7558128e41a1

Source dataset

uspto-grants-2010_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07858796B2