Potassium Carbonate → HCID 86650780, compound

HRID 1893527Notes

Reaction equation

HRID 1893527 reaction equation
Cl.[C:2]1([C@@H:8]2[CH2:10][C@H:9]2[NH2:11])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:12](=O)([O-])[O-:13].[K+].[K+]>O>[C:2]1([C@@H:8]2[CH2:10][C@H:9]2[NH:11][CH:12]=[O:13])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 2723716Tranylcypromine hydrochloride

Product 1

HCID 86650780HCID 86650780, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

trans-2-Phenylcyclopropylamine hydrochloride (2.74 g, 16.15 mmol) was dissolved in water (50 ml), and the solution was alkalified with potassium carbonate. The mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the solution was concentrated under reduced pressure. To the residue was added formic acid (18.5 ml), and the mixture was ice-cooled, and acetic anhydride (7 ml) was added dropwise with stirring. The reaction mixture was stood at room temperature overnight, ice-cooled again. Water (7 ml) was added, and the mixture was concentrated under reduced pressure. The residue was diluted with ethyl acetate, washed with 5% aqueous potassium carbonate solution and saturated brine, and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the solution was concentrated under reduced pressure to give the title compound (2.36 g, yield 91%) as a pale-bistered solid.

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationThe insoluble material was filtered off
  5. concentrationthe solution was concentrated under reduced pressure
  6. additionTo the residue was added formic acid (18.5 ml)
  7. temperaturecooled
  8. additionacetic anhydride (7 ml) was added dropwise
  9. temperatureice-cooled again
  10. additionWater (7 ml) was added
  11. concentrationthe mixture was concentrated under reduced pressure
  12. additionThe residue was diluted with ethyl acetate
  13. washwashed with 5% aqueous potassium carbonate solution and saturated brine
  14. dry with materialdried over anhydrous magnesium sulfate
  15. filtrationThe insoluble material was filtered off
  16. concentrationthe solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-2814e5cd6a7e4493b7e147e127fc0fbf
Source dataset
uspto-grants-2013_08
Patent number
US08513235B2

Reaction notes

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