Potassium Carbonate → HCID 22329033, compound

HRID 587092Notes

Reaction equation

HRID 587092 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH2:12][CH2:13][CH3:14])[CH2:10][CH2:9][CH2:8][C:7](=[O:15])[C:6]=2[CH:16]=1.B([O-])([O-])O[C:19]1[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][O:28][CH2:29][CH2:30][CH2:31][CH3:32])=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C(CCO)=CC=CC=1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:29]([O:28][CH2:27][CH2:26][O:25][C:22]1[CH:21]=[CH:20][C:19]([C:2]2[CH:3]=[CH:4][C:5]3[N:11]([CH2:12][CH2:13][CH3:14])[CH2:10][CH2:9][CH2:8][C:7](=[O:15])[C:6]=3[CH:16]=2)=[CH:24][CH:23]=1)[CH2:30][CH2:31][CH3:32]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 22329115HCID 22329115, compoundHCID 867568154-Butoxyethoxyphenyl borate

Product 1

HCID 22329033HCID 22329033, compoundYield 86.6%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 66602552Toluene-ethanol waterSolvent

Procedure

A mixture of 7-bromo-1-propyl-2,3,4,5-tetrahydro-1H-1-benzazepine-5-one (5.89 g), 4-(2-butoxyethoxy)phenyl borate (5.45 g) and potassium carbonate (5.74 g) in toluene-ethanol-water (200-20-20 ml) was stirred at room temperature for 1 hour under argon atmosphere. To the reaction system was added tetrakistriphenylphosphinepalladium (0.72 g), and the mixture was heated to reflux for 3 hours. After cooled to room temperature, the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried with magnesium sulfate. After concentration under reduced pressure, the residue was separated and purified with column chromatography (ethyl acetate:hexane=1:9→1:4) to give 7-[4-(2-butoxyethoxy)phenyl]-1-propyl-2,3,4,5-tetrahydro-1H-1-benzazepine-5-one (7.15 g) as yellow oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 3 hours
  3. temperatureAfter cooled to room temperature
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried with magnesium sulfate
  7. concentrationAfter concentration under reduced pressure
  8. customthe residue was separated
  9. custompurified with column chromatography (ethyl acetate:hexane=1:9→1:4)

Sources & evidence

ORD record
ord-462c4ba1925648e084f208cc273c54ad
Source dataset
uspto-grants-2005_08
Patent number
US06936602B1

Reaction notes

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