5-benzyl-10-fluoro-5H-dibenz[b,f]azepine → 10-fluoro-5H-dibenz[b,f]azepine

HRID 616885

Reaction equation

HRID 616885 reaction equation
C([N:8]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[C:12]([F:19])=[CH:11][C:10]2[CH:20]=[CH:21][CH:22]=[CH:23][C:9]1=2)C1C=CC=CC=1.[H][H]>CO.[Pd]>[F:19][C:12]1[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[NH:8][C:9]2[CH:23]=[CH:22][CH:21]=[CH:20][C:10]=2[CH:11]=1

Participants

5

Reactant 2

HCID 203664075-benzyl-10-fluoro-5H-dibenz[b,f]azepineHCID 178418361HCID 178418361, compound

Product 1

HCID 2036640810-fluoro-5H-dibenz[b,f]azepine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 6.03 g (0.02 mole) of 5-benzyl-10-fluoro-5H-dibenz[b,f]azepine in 100 ml of methanol is hydrogenated at 25° C in the presence of 0.6 of palladium on charcoal catalyst (5% Pd) until the uptake of hydrogen has ceased (app. 15 hours). The catalyst is filtered off and the filtrate is concentrated in vacuo. The residual colourless oil is chromatographed over 50 times the amount of silica gel (particle size: 0.063-0.2 mm) with benzene/petroleum ether (1:1) as eluant. The homogeneous fractions are combined, concentrated by rotary evaporation and the residue is crystallised from ether/hexane to yield 10-fluoro-5H-dibenz[b,f]azepine of m.p. 69°-72° C.

Workup

  1. custom(app. 15 hours)
  2. filtrationThe catalyst is filtered off
  3. concentrationthe filtrate is concentrated in vacuo
  4. customThe residual colourless oil is chromatographed over 50 times the amount of silica gel (particle size: 0.063-0.2 mm) with benzene/petroleum ether (1:1) as eluant
  5. concentrationconcentrated by rotary evaporation
  6. customthe residue is crystallised from ether/hexane

Sources & evidence

ORD record
ord-ade755ed64bf4eb488dae0d3cae1edfe
Source dataset
uspto-grants-1978_02
Patent number
US04076812

Linked notes

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