Ethyl bromoacetate → HCID 53861417, compound

HRID 1683763Notes

Reaction equation

HRID 1683763 reaction equation
[H-].[K+].[Cl:3][C:4]1[C:9]2[CH2:10][CH2:11][N:12]([CH3:15])[CH2:13][CH2:14][C:8]=2[C:7]([OH:16])=[CH:6][CH:5]=1.Br[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20]>CN(C)C=O>[Cl:3][C:4]1[C:9]2[CH2:10][CH2:11][N:12]([CH3:15])[CH2:13][CH2:14][C:8]=2[C:7]([O:16][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 82127Potassium hydrideHCID 133383339-Chloro-3-methyl-2,3,4,5-tetrahydro-1H-3-benzazepin-6-ol

Product 1

HCID 53861417HCID 53861417, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A 35% dispersion of potassium hydride in mineral oil (2.6 g, 23 mmol) in dimethylformamide (40 ml) was stirred and treated with 9-chloro-2,3,4,5-tetrahydro-3-methyl-1H-3-benzazepin-6-ol (4.0 g, 19 mmol), stirred for 20 minutes, treated with ethyl bromoacetate (3.8 g, 23 mmol) and stirred for 72 hours. The mixture was concentrated, partitioned between water and methylene chloride and the organic phase was washed, dried with magnesium sulfate and concentrated. The residue was chromatographed on silica gel eluted with methanol-methylene chloride (8:92) to give 4.3 g of ethyl [(9-chloro-2,3,4,5-tetrahydro-3-methyl-1H-3-benzazepin-6-yl)oxy]acetate.

Workup

  1. stirringstirred for 72 hours
  2. concentrationThe mixture was concentrated
  3. custompartitioned between water and methylene chloride
  4. washthe organic phase was washed
  5. dry with materialdried with magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue was chromatographed on silica gel
  8. washeluted with methanol-methylene chloride (8:92)

Sources & evidence

ORD record
ord-8c6351e952dd4a23978145d5122f121a
Source dataset
uspto-grants-1997_06
Patent number
US05639748

Reaction notes

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