Cesium carbonate → HCID 58492480, compound

HRID 68133Notes

Reaction equation

HRID 68133 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[O:11][CH2:12][CH2:13][CH3:14])[CH2:7][CH2:6][CH2:5]2.C(=[NH:28])(C1C=CC=CC=1)C1C=CC=CC=1.CC1(C)C2C=CC=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=2OC2C1=CC=CC=2P(C1C=CC=CC=1)C1C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].[Cl-].[NH4+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O>[CH2:12]([O:11][C:10]1[CH:9]=[C:8]2[C:4]([CH2:5][CH2:6][CH2:7]2)=[CH:3][C:2]=1[NH2:28])[CH2:13][CH3:14]

Participants

8

Reactant 5

HCID 10796Cesium carbonateHCID 25517Ammonium ChlorideHCID 136809Benzophenone imineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 58492585HCID 58492585, compound

Product 1

HCID 58492480HCID 58492480, compoundYield 17%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To a 5-bromo-6-propoxyindan (8.24 g, 32.2 mmol) toluene solution (80 ml) were added a benzophenone imine (6.40 g, 35.3 mmol) toluene solution (40 ml), tris(dibenzylideneacetone)dipalladium (742 mg, 0.8 mmol), 9,9-dimethyl-4,5-bis (diphenylphosphino)xanthene (XANTPHOS, 936 mg, 1.6 mmol), and cesium carbonate (15.72 g, 48.3 mmol). The resulting mixture was stirred at 100° C. under a nitrogen atmosphere for 47 hours, and then cooled to room temperature. Water and saturated ammonium chloride solution were added to the reaction mixture, followed by extraction using ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and then concentrated to dryness under reduced pressure. The generated residue was dissolved in diethyl ether (130 ml). Concentrated hydrochloric acid (25 ml) was added to the solution, followed by stirring for 2 hours. A 5N aqueous sodium hydroxide solution (72 ml) was added to the reaction mixture to adjust its pH to 11, followed by concentration under reduced pressure. The residue was dissolved in dichloromethane and washed with an aqueous saturated sodium chloride solution. The thus-obtained organic layer was concentrated to dryness under reduced pressure, and the generated residue was then purified using silica gel column chromatography (dichloromethane:ethyl acetate=90:1). The purified product was concentrated to dryness under reduced pressure, giving a pale brown oily substance of 6-propoxy-indan-5-ylamine (1.02 g, yield: 17%).

Workup

  1. temperaturecooled to room temperature
  2. extractionfollowed by extraction
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated to dryness under reduced pressure
  5. dissolutionThe generated residue was dissolved in diethyl ether (130 ml)
  6. additionConcentrated hydrochloric acid (25 ml) was added to the solution
  7. stirringby stirring for 2 hours
  8. additionA 5N aqueous sodium hydroxide solution (72 ml) was added to the reaction mixture
  9. concentrationfollowed by concentration under reduced pressure
  10. dissolutionThe residue was dissolved in dichloromethane
  11. washwashed with an aqueous saturated sodium chloride solution
  12. concentrationThe thus-obtained organic layer was concentrated to dryness under reduced pressure
  13. customthe generated residue was then purified
  14. concentrationThe purified product was concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-94b6820247ad40a4a540fe0a60a08279
Source dataset
uspto-grants-2014_09
Patent number
USRE045108E1

Reaction notes

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