Benzyl Bromide → HCID 59403479, compound

HRID 1514194Notes

Reaction equation

HRID 1514194 reaction equation
[OH:1][C:2]1[CH:13]=[CH:12][C:5]2[C:6](=[O:11])[NH:7][CH2:8][CH2:9][O:10][C:4]=2[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.CCOC(C)=O.O>[C:15]1([CH2:14][O:1][C:2]2[CH:13]=[CH:12][C:5]3[C:6](=[O:11])[NH:7][CH2:8][CH2:9][O:10][C:4]=3[CH:3]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 59403478HCID 59403478, compound

Product 1

HCID 59403479HCID 59403479, compoundYield 64.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 22728543Water ethylacetateSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 8-hydroxy-3,4-dihydro-1,4-benzoxazepin-5(2H)-one (Preparation 26) (8.66 g, 48.3 mmol), benzyl bromide (6.32 ml, 53.2 mmol) and potassium carbonate (20.04 g, 145 mmol) in DMF (80 ml) was stirred and heated at 60° C. for 2 hours. The cooled reaction was diluted with EtOAc/water (300 ml of each) and the aqueous extracted with EtOAc (2×75 ml). Combined organics were washed with 3×100 ml of water, dried (magnesium sulphate), evaporated, triturated with ether and filtered off to give the title compound (8.39 g) as a white solid. MS (ES) C16H15NO3 requires 269; found 270 [M+H]+.

Workup

  1. customThe cooled reaction
  2. extractionaqueous extracted with EtOAc (2×75 ml)
  3. washCombined organics were 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-6d70ed0ce0d54547afd7bd62edeb6c19
Source dataset
uspto-grants-2012_07
Patent number
US08222245B2

Reaction notes

Loading…