Formic Acid → HCID 67303719, compound

HRID 1951480Notes

Reaction equation

HRID 1951480 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=1[NH:12][CH:13]1[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]1.[C:26]([BH3-])#N.[Na+].C(O)=O.C=O.C(=O)(O)[O-].[Na+]>O.CO>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=1[N:12]([CH3:26])[CH:13]1[CH2:14][CH2:15][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:17][CH2:18]1

Participants

8

Reactant 5

HCID 284Formic AcidHCID 712FormaldehydeHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 67303179HCID 67303179, compound

Product 1

HCID 67303719HCID 67303719, compoundYield 112.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
27.5 °C

Procedure

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.

Workup

  1. customobtained at step (I) into a round bottom flask
  2. customWhite solid mass separated out
  3. temperatureThen the reaction mass was cooled to 0-5° C. in an ice bath
  4. customA clear solution was obtained
  5. stirringThe mass was further stirred for 6 hours at 20-25° C
  6. customAfter completion of reaction (thin layer chromatography), solvent
  7. distillationwas distilled off
  8. customto obtain oily mass
  9. extractionExtracted the product with ethyl acetate (3×100 mL) and layers
  10. customseparated
  11. washThe combined organic layer was washed with brine solution (100 mL)
  12. dry with materialdried over anhydrous sodium sulfate
  13. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-afbb628126044ca185017af5fca57c8d
Source dataset
uspto-grants-2013_03
Patent number
US08404720B2

Reaction notes

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