Hydrochloric Acid → 697305-72-9

Iron (1.36 g, 21.9 mmol) and concentrated hydrochloric acid (0.15 mL) was added to ethanol/water (20 mL/20 mL), followed by refluxing for 1 hour. The mixed reaction solution was added with 1-(2-chloro-5-nitrophenyl)-N,N-dimethylmethanamine (940 mg, 4.38 mmol) obtained in <Step 1> above, and refluxed for 1 hour. The reaction mixture was filtered through a Celite pad under reduced pressure, and washed with ethanol and chloroform/2-propanol=3/1 (v/v). The resulting filtrate was distilled under reduced pressure, and dissolved in ethyl acetate. The organic layer formed was washed with an aqueous solution of sodium bicarbonate and brine. The obtained organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The concentrated compound was purified using silica gel chromatography (chloroform:methanol=30:1→15:1 (v/v)) to obtain the title compound (442 mg, 55%).

1. temperatureby refluxing for 1 hour
2. customThe mixed reaction solution
3. customobtained in <Step 1> above, and
4. temperaturerefluxed for 1 hour
5. filtrationThe reaction mixture was filtered through a Celite pad under reduced pressure
6. washwashed with ethanol and chloroform/2-propanol=3/1 (v/v)
7. distillationThe resulting filtrate was distilled under reduced pressure
8. dissolutiondissolved in ethyl acetate
9. customThe organic layer formed
10. washwas washed with an aqueous solution of sodium bicarbonate and brine
11. dry with materialThe obtained organic layer was dried over anhydrous sodium sulfate
12. filtrationfiltered
13. concentrationconcentrated under reduced pressure
14. customThe concentrated compound was purified

ORD record

ord-eeb5f0572dbd4ecdad130f6af017356d

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09156852B2