Water → HCID 21349894, compound

HRID 2186736Notes

Reaction equation

HRID 2186736 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[C:10]2[CH:11]=[CH:12][CH:13]=[C:14]([OH:15])[C:9]=2[CH2:8][CH2:7][CH2:6][CH2:5]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:23][C:24]([O:26][CH3:27])=[O:25].O>CN(C=O)C>[OH:1][CH2:2][CH2:3][N:4]1[C:10]2[CH:11]=[CH:12][CH:13]=[C:14]([O:15][CH2:23][C:24]([O:26][CH3:27])=[O:25])[C:9]=2[CH2:8][CH2:7][CH2:6][CH2:5]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 22449061HCID 22449061, compound

Product 1

HCID 21349894HCID 21349894, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-(2-hydroxyethyl)-6-hydroxy-2,3,4,5-tetrahydro-1H-1-benzazepine (52 mg) was dissolved in DMF (3 ml), and the resultant solution was stirred at room temperature. Potassium carbonate (122 mg) and methyl bromoacetate (0.035 ml) were added to the solution, and the mixture was stirred at room temperature. After disappearance of the raw materials was confirmed, water (20 ml) was added to the reaction solution, and the mixture was then extracted with ethyl acetate. The resultant organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and then concentrated. The resultant residue was purified by column chromatography (silica gel:hexane/ethyl acetate=2/1) to obtain the object compound (47 mg, yield 67%).

Workup

  1. extractionthe mixture was then extracted with ethyl acetate
  2. washThe resultant organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe resultant residue was purified by column chromatography (silica gel:hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-7cb5eb0699e7454d9bca028e45007d70
Source dataset
uspto-grants-2002_06
Patent number
US06407096B1

Reaction notes

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