HCID 20366413, compound → HCID 13345369, compound

HRID 616888Notes

Reaction equation

HRID 616888 reaction equation
[Br:1][C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6](C(=O)C(F)(F)F)[C:5]2[CH:19]=[CH:20][CH:21]=[CH:22][C:4]=2[CH:3]=1>CO.[OH-].[Na+].O>[Br:1][C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[NH:6][C:5]2[CH:19]=[CH:20][CH:21]=[CH:22][C:4]=2[CH:3]=1

Participants

5

Reactant 1

HCID 20366413HCID 20366413, compound

Product 1

HCID 13345369HCID 13345369, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 85.9 g of 10-bromo-5-(trifluoroacetyl)-5H-dibenz[b,f]azepine in 500 ml of methanol and 233 ml of normal sodium hydroxide solution is refluxed for 2 hours. The methanol is evaporated off, the concentrated reaction mixture diluted with water and extracted with ethyl acetate. The organic phase is washed with saturated sodium chloride solution, dried over magnesium sulphate and concentrated by evaporation. The residue is purified by chromatography over 380 g of silica gel with benzene/petroleum ether (1:1) as eluant. The fraction containing pure 10-bromo-5H-dibenz[b,f]azepine are combined and concentrated by evaporation. The residue is crystallised from cyclohexane to yield 10-bromo-5H-dibenz[b,f]azepine which melts at 65°-69° C.

Workup

  1. customThe methanol is evaporated off
  2. customthe concentrated reaction mixture
  3. extractionextracted with ethyl acetate
  4. washThe organic phase is washed with saturated sodium chloride solution
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated by evaporation
  7. customThe residue is purified by chromatography over 380 g of silica gel with benzene/petroleum ether (1:1) as eluant
  8. additionThe fraction containing pure 10-bromo-5H-dibenz[b,f]azepine
  9. concentrationconcentrated by evaporation
  10. customThe residue is crystallised from cyclohexane

Sources & evidence

ORD record
ord-e8e72d70ac314d38b9242e1f1475371f
Source dataset
uspto-grants-1978_02
Patent number
US04076812

Reaction notes

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