Formic Acid → HCID 67309659, compound

Temperature

27.5 °C

To a 250 mL three neck round bottom flask added 2-Methoxy-5-nitro-N-methyl-N-(piperidin-4-yl) phenylamine (1.93 grams, 7.33 mmol) obtained at step (III), followed by the addition of methanol (20 mL) and stirred at 25-30° C. for 5 minutes. Added sodium cyanoborohydride (0.548 grams, 8.80 mmol) and formic acid (1.08 mL, 22.01 mmol) and stirred the reaction mass for 10 minutes. The reaction mass was cooled to 0-5° C. in an ice bath and added formaldehyde (1.46 mL, 14.6 mmol, 30-50%) through syringe. Clear solution was obtained. The reaction mass was further stirred for 6 hours at 20-25° C. After completion of reaction (thin layer chromatography), solvent was distilled off under reduced pressure. To the residual oily mass, added water (100 mL) and basified to pH: 8 using saturated solution of sodium bicarbonate. The product was extracted with ethyl acetate (3×100 mL). The combined organic layer was washed with brine solution (100 mL) and dried over anhydrous sodium sulfate. Solvent was removed under reduced pressure to obtain 1.96 grams of dark yellow colored oily mass.

1. customobtained at step (III)
2. temperatureThe reaction mass was cooled to 0-5° C. in an ice bath
3. customClear solution was obtained
4. stirringThe reaction mass was further stirred for 6 hours at 20-25° C
5. customAfter completion of reaction (thin layer chromatography), solvent
6. distillationwas distilled off under reduced pressure
7. additionTo the residual oily mass, added water (100 mL)
8. extractionThe product was extracted with ethyl acetate (3×100 mL)
9. washThe combined organic layer was washed with brine solution (100 mL)
10. dry with materialdried over anhydrous sodium sulfate
11. customSolvent was removed under reduced pressure
12. customto obtain 1.96 grams of dark yellow colored oily mass

ORD record

ord-69cc6714e8b3453ca06e405dee34993a

Source dataset

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08404720B2