Formic Acid → HCID 67303719, compound

Participants

Reaction Conditions

Reaction Steps

Placed 2-Methoxy-5-nitro-N-(1-Boc piperidin-4-yl)phenylamine (5 grams, 14.24 mmol) obtained at step (I) into a round bottom flask containing methanol (10 mL) and stirred at 25-30° C. for 5 minutes. Added sodium cyanoborohydride (1.06 grams, 17.09 mmol) and formic acid (1.96 grams, 42.7 mmol) and stirred the reaction mass for 10 minutes. White solid mass separated out. Then the reaction mass was cooled to 0-5° C. in an ice bath and added formaldehyde (2.84 mL, 28.4 mmol, 30-50%). A clear solution was obtained. The mass was further stirred for 6 hours at 20-25° C. After completion of reaction (thin layer chromatography), solvent was distilled off to obtain oily mass. Added water (100 mL) and basified to pH: 8 using saturated solution of sodium bicarbonate solution. Extracted the product with ethyl acetate (3×100 mL) and layers separated. The combined organic layer was washed with brine solution (100 mL) and dried over anhydrous sodium sulfate. The organic layer was concentrated to obtain 5.86 grams of dark yellow colored oil.

Provenance & Evidence