Formic Acid → 14446-29-8

HRID 352855Notes

Reaction equation

HRID 352855 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[CH2:6][CH2:7][NH2:8].[CH:12](O)=O.C(OC(=O)C)(=O)C.C(=O)(O)[O-].[Na+]>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[CH:12]=[N:8][CH2:7][CH2:6]2

Participants

6

Reactant 4

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 748663-MethoxyphenethylamineHCID 516892Sodium Bicarbonate

Product 1

HCID 1001219614446-29-8

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In tetrahydrofuran (100 ml), 3-methoxyphenethylamine (75.0 g) was dissolved. To the resulting solution, formic acid (60 ml) and acetic anhydride (108 ml) were added under ice cooling, followed by stirring overnight at room temperature. A saturated aqueous solution of sodium bicarbonate was added to the reaction mixture to separate the organic layer. The organic layer was washed with saturated aqueous NaCl solution and then dried over anhydrous sodium sulfate. The residue obtained by distilling off the solvent under reduced pressure was dissolved in benzene (200 ml), followed by the dropwise addition of phosphorus oxychloride (140 ml) under ice cooling. After stirring at 70° C. for 15 minutes, the reaction mixture was successively added with ice and 2N hydrochloric acid. The resulting mixture was stirred for 1 hour under ice cooling. The water layer was separated from the reaction mixture, neutralized with potassium carbonate and then extracted with dichloromethane. The extract was dried over anhydrous sodium sulfate. The residue obtained by distilling off the solvent under reduced pressure was purified by chromatography on a silica gel column (dichloromethane˜dichloromethane:methanol=100:1), whereby the title compound (13.5 g, 17%) was obtained.

Workup

  1. customto separate the organic layer
  2. washThe organic layer was washed with saturated aqueous NaCl solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe residue obtained
  5. distillationby distilling off the solvent under reduced pressure
  6. dissolutionwas dissolved in benzene (200 ml)
  7. additionfollowed by the dropwise addition of phosphorus oxychloride (140 ml) under ice cooling
  8. stirringAfter stirring at 70° C. for 15 minutes
  9. additionthe reaction mixture was successively added with ice and 2N hydrochloric acid
  10. stirringThe resulting mixture was stirred for 1 hour under ice cooling
  11. customThe water layer was separated from the reaction mixture
  12. extractionextracted with dichloromethane
  13. dry with materialThe extract was dried over anhydrous sodium sulfate
  14. customThe residue obtained
  15. distillationby distilling off the solvent under reduced pressure
  16. customwas purified by chromatography on a silica gel column (dichloromethane˜dichloromethane:methanol=100:1), whereby the title compound (13.5 g, 17%)
  17. customwas obtained

Sources & evidence

ORD record
ord-29c15f034c2c49378bc882737d07dcac
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

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