Cyanogen Bromide → cis-8-fluoro-1,3,4,4a,5,10b-hexahydro-2H-benzo[h]isoquinolin-6-one

HRID 382813Notes

Reaction equation

HRID 382813 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:14]3[CH:9]([CH2:10][CH2:11][N:12](C)[CH2:13]3)[CH2:8][C:7](=[O:16])[C:6]=2[CH:17]=1.N#CBr>C(Cl)(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[C@H:14]3[C@H:9]([CH2:10][CH2:11][NH:12][CH2:13]3)[CH2:8][C:7](=[O:16])[C:6]=2[CH:17]=1

Participants

4

Reactant 2

HCID 10476Cyanogen BromideHCID 18361940HCID 18361940, compound

Product 1

HCID 86757545cis-8-fluoro-1,3,4,4a,5,10b-hexahydro-2H-benzo[h]isoquinolin-6-oneYield 69%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

0.45 g (1.92 mmol) of 8-fluoro-2-methyl-1,3,4,4a,5,10b-hexahydro-2H-benzo[h]isoquinolin-6-one was dissolved in 6 ml of anhydrous chloroform and added dropwise at room temperature over 15 minutes to a solution of 244 mg (2.3 mmol) of cyanogen bromide in 2 ml of anhydrous chloroform. Subsequently, the mixture was heated under reflux for a further 75 minutes, concentrated in a vacuum, taken up with 12 ml of 2N hydrochloric acid and heated under reflux over 6 hours. Subsequently, the mixture was made basic with 3N sodium hydroxide solution and extracted three times with 50 ml of diethyl ether each time. The combined organic phases were washed once with 70 ml of saturated sodium chloride solution, dried (MgSO4) and concentrated in a vacuum. 0.29 g (69%) of cis-8-fluoro-1,3,4,4a,5,10b-hexahydro-2H-benzo[h]isoquinolin-6-one was obtained as a yellow oil.

Workup

  1. temperatureSubsequently, the mixture was heated
  2. temperatureunder reflux for a further 75 minutes
  3. concentrationconcentrated in a vacuum
  4. temperatureheated
  5. temperatureunder reflux over 6 hours
  6. extractionextracted three times with 50 ml of diethyl ether each time
  7. washThe combined organic phases were washed once with 70 ml of saturated sodium chloride solution
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated in a vacuum

Sources & evidence

ORD record
ord-0412261645784c1ab80ca1f10b87f854
Source dataset
uspto-grants-2001_10
Patent number
US06310208B1

Reaction notes

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