Water → 2,3,4,5-Tetrahydro-7-(phenylmethoxy)-1H-2-benzazepin-1-one

HRID 393564Notes

Reaction equation

HRID 393564 reaction equation
[C:1](=[O:4])([O-])[O-].[K+].[K+].[CH2:7](Br)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O.[CH3:16][N:17](C)[CH:18]=[O:19]>>[CH2:7]([O:4][C:1]1[CH:11]=[CH:10][C:9]2[C:18](=[O:19])[NH:17][CH2:16][CH2:12][CH2:13][C:8]=2[CH:7]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 11430Potassium Carbonate

Product 1

HCID 222380502,3,4,5-Tetrahydro-7-(phenylmethoxy)-1H-2-benzazepin-1-one

Procedure

Under atmosphere of argon, to a solution of the compound prepared in reference example 5 (4.79 g) in dimethylformamide (60 ml) were added potassium carbonate (11.2 g) and benzyl bromide (3.57 ml) at 0° C. and the mixture was stirred for 30 minutes at room temperature. To the reaction mixture was added water and was extracted with ethyl acetate. The organic layer was washed with water, a saturated aqueous solution of sodium bicarbonate and a saturated aqueous solution of sodium chloride successively, and was dried over anhydrous magnesium sulfate and was concentrated. The residue was purified by column chromatography on silica gel (ethyl acetate:n-hexane=3:1) to give the title compound (3.8 g) having the following physical data.

Workup

  1. extractionwas extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materiala saturated aqueous solution of sodium bicarbonate and a saturated aqueous solution of sodium chloride successively, and was dried over anhydrous magnesium sulfate
  4. concentrationwas concentrated
  5. customThe residue was purified by column chromatography on silica gel (ethyl acetate:n-hexane=3:1)

Sources & evidence

ORD record
ord-19939fcb9cc949e7acd7e0bd7d6cf08b
Source dataset
uspto-grants-2004_10
Patent number
US06809092B2

Reaction notes

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