Water → HCID 22329025, compound

HRID 586915Notes

Reaction equation

HRID 586915 reaction equation
[C:1](Cl)(=[O:4])[CH2:2][CH3:3].[CH2:6]([O:9][CH2:10][CH2:11][O:12][C:13]1[CH:14]=[CH:15][C:16]2[NH:22][CH2:21][CH2:20][C:19]([C:23]([O:25][CH3:26])=[O:24])=[CH:18][C:17]=2[CH:27]=1)[CH2:7][CH3:8].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[C:1]([N:22]1[C:16]2[CH:15]=[CH:14][C:13]([O:12][CH2:11][CH2:10][O:9][CH2:6][CH2:7][CH3:8])=[CH:27][C:17]=2[CH:18]=[C:19]([C:23]([O:25][CH3:26])=[O:24])[CH2:20][CH2:21]1)(=[O:4])[CH2:2][CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 62324Propionyl chlorideHCID 22328948HCID 22328948, compound

Product 1

HCID 22329025HCID 22329025, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Propionyl chloride (1.0 ml) was added dropwise to a suspension of methyl 7-(2-propoxyethoxy)-2,3-dihydro-1H-1-benzazepine-4-carboxylate (0.2 g) and potassium carbonate (2.2 g) in DMF (10 ml) under ice-cooling. The mixture was stirred at room temperature overnight under nitrogen atmosphere, and poured into water, which was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried with anhydrous magnesium sulfate. The solvent was evaporated and the residue was purified with silica gel column chromatography (ethyl acetate/hexane) to give methyl 1-propionyl-7-(2-propoxyethoxy)-2,3-dihydro-1H-1-benzazepine-4-carboxylate (0.2 g) as pale yellow oil.

Workup

  1. temperaturecooling
  2. extractionwas extracted with ethyl acetate
  3. washThe organic layer was washed with water and saturated brine
  4. dry with materialdried with anhydrous magnesium sulfate
  5. customThe solvent was evaporated
  6. customthe residue was purified with silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-8eec81d3e60b4dbf8829ac3db5ffaf08
Source dataset
uspto-grants-2005_08
Patent number
US06936602B1

Reaction notes

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