Hydrochloric Acid → HCID 67323243, compound

Temperature

130 °C

A mixture of 1.00 g (5.21 mmol) of 2,5-dichloronitrobenzene and 1.01 g (7.81 mmol) of 4-piperdineethanol in N,N-dimethylformamide (3 mL) is heated at 130° C. and stirred overnight. The mixture is cooled to room temperature, diluted with water and extracted with ethyl acetate. The combined organic phase is washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to provide a red oil. The residue is dissolved in ethanol (15 mL) and 0.20 g (0.19 mmol) of 10% palladium on carbon is added followed by a drop of concentrated hydrochloric acid. The mixture is stirred at room temperature for 2 hours then filtered through a pad of diatomaceous earth and the filter pad is washed with methanol. The mixture is concentrated under reduced pressure to provide a black oil. The residue is dissolved in acetonitrile (50 mL) and treated with 1.03 g (5.89 mmol) of 3-chlorobenzoyl chloride. The mixture is stirred at room temperature for 3 hours then concentrated under reduced pressure. To the residue is slowly added a 2M solution of sodium bicarbonate. The mixture is extracted with ethyl acetate and the combined organic phase is washed with brine and dried over anhydrous sodium sulfate. The mixture is concentrated and the residue is purified by flash silica gel chromatography to give 0.800 g (39.0% overall) of 3-chloro-N-{5-chloro-2-[4-(2-hydroxy-ethyl)-piperidin-1-yl]-phenyl}-benzamide as a brown foam.

1. temperatureThe mixture is cooled to room temperature
2. extractionextracted with ethyl acetate
3. washThe combined organic phase is washed with brine
4. dry with materialdried over anhydrous sodium sulfate
5. concentrationconcentrated under reduced pressure
6. customto provide a red oil
7. stirringThe mixture is stirred at room temperature for 2 hours
8. filtrationthen filtered through a pad of diatomaceous earth
9. washthe filter pad is washed with methanol
10. concentrationThe mixture is concentrated under reduced pressure
11. customto provide a black oil
12. stirringThe mixture is stirred at room temperature for 3 hours
13. concentrationthen concentrated under reduced pressure
14. additionTo the residue is slowly added a 2M solution of sodium bicarbonate
15. extractionThe mixture is extracted with ethyl acetate
16. washthe combined organic phase is washed with brine
17. dry with materialdried over anhydrous sodium sulfate
18. concentrationThe mixture is concentrated
19. customthe residue is purified by flash silica gel chromatography

ORD record

ord-703085f82455480da29892fac456e095

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08952004B2