Benzyl Bromide → 9-[(Phenylmethyl)oxy]-3,4-dihydro-1,4-benzoxazepin-5(2H)-one

HRID 1514220Notes

Reaction equation

HRID 1514220 reaction equation
[OH:1][C:2]1[C:12]2[O:11][CH2:10][CH2:9][NH:8][C:7](=[O:13])[C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[C:15]1([CH2:14][O:1][C:2]2[C:12]3[O:11][CH2:10][CH2:9][NH:8][C:7](=[O:13])[C:6]=3[CH:5]=[CH:4][CH:3]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 594035349-Hydroxy-3,4-dihydro-1,4-benzoxazepin-5(2H)-one

Product 1

HCID 594034959-[(Phenylmethyl)oxy]-3,4-dihydro-1,4-benzoxazepin-5(2H)-oneYield 67.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 9-hydroxy-3,4-dihydro-1,4-benzoxazepin-5(2H)-one (7.46 g, 41.6 mmol), benzyl bromide (Preparation 58) (5.45 ml, 45.8 mmol) and potassium carbonate (17.26 g, 125 mmol) was stirred and heated at 60° C. in DMF (75 ml) for 2 hours. Cooled, diluted with water (300 ml) and extracted with EtOAc (200 ml and 4×75 ml) and the combined organics washed with 3×100 ml of water. Dried (magnesium sulphate), evaporated, triturated with ether and filtered off to give 7.55 g of white solid. MS (ES): C16H15NO3 requires 269; found 270 [M+H]+.

Workup

  1. temperatureCooled
  2. extractionextracted with EtOAc (200 ml and 4×75 ml)
  3. washthe combined organics washed with 3×100 ml of water
  4. dry with materialDried (magnesium sulphate)
  5. customevaporated
  6. customtriturated with ether
  7. filtrationfiltered off

Sources & evidence

ORD record
ord-580979ea23a343258aa1d1a96212ed95
Source dataset
uspto-grants-2012_07
Patent number
US08222245B2

Reaction notes

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