Formic Acid → 14446-29-8

HRID 1061039Notes

Reaction equation

HRID 1061039 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 1001219614446-29-8Yield 17%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In tetrahydrofuran (100 ml), 3-methoxyphenethylamine (75.0 g) was dissolved, followed by the addition of formic acid (60 ml) and acetic anhydride (108 ml) under ice cooling. The resulting mixture was stirred overnight at room temperature. A saturated aqueous solution of sodium bicarbonate was added to the reaction mixture. The organic lay-layer so separated was washed with saturated saline and 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, ice and then 2N hydrochloric acid were added. The resulting mixture was stirred under ice cooling for one hour. The water layer was separated and neutralized with potassium carbonate. After extraction 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), the title compound (13.5 g, 17%) was obtained.

Workup

  1. customThe organic lay-layer so separated
  2. washwas washed with saturated saline
  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. additionice and then 2N hydrochloric acid were added
  10. stirringThe resulting mixture was stirred under ice cooling for one hour
  11. customThe water layer was separated
  12. extractionAfter extraction 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)

Sources & evidence

ORD record
ord-ad2203be60a8412ba086f7f795772441
Source dataset
uspto-grants-2003_02
Patent number
US06525042B1

Reaction notes

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