Cyanogen Bromide → HCID 54212508, compound

HRID 2248112Notes

Reaction equation

HRID 2248112 reaction equation
[N:1]#CBr.[CH3:4][N:5]1[C:9]2[CH2:10][CH2:11][C:12]3[C:19]4([CH3:22])[CH:20]([CH3:21])[CH:6]1[CH2:7][C:8]=2[C:13]=3[CH:14]=[CH:15][CH2:16][N:17]=[CH:18]4.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[C:4]([N:5]1[C:9]2[CH2:10][CH2:11][C:12]3[C:19]4([CH3:22])[CH:20]([CH3:21])[CH:6]1[CH2:7][C:8]=2[C:13]=3[CH:14]=[CH:15][CH2:16][N:17]=[CH:18]4)#[N:1]

Participants

5

Reactant 3

HCID 10476Cyanogen BromideHCID 516892Sodium BicarbonateHCID 54133654HCID 54133654, compound

Product 1

HCID 54212508HCID 54212508, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a stirred solution of 0.50 g of cyanogen bromide and 20 ml of chloroform was added, at room temperature with stirring, a solution of 1.0 g of 1,2,3,4,5,6-hexahydro-3,6,12-trimethyl-2,6-methano-9H-pyrrolo[3,2-h][3]benzazocine and 40 ml of chloroform. The mixture was heated at reflux for 2.6 hr, under nitrogen, and then cooled to room temperature. Dilute aqueous sodium bicarbonate solution was added and the layers were separated. The organic layer was washed with sodium bicarbonate solution. The combined aqueous layers were back extracted with ether, and the combined organic layers were washed with brine, dried over anhydrous potassium carbonate and filtered. The filtrate was concentrated. The residue was purified by flash chromatography (silica gel, 2% triethylamine/ether) to afford 0.73 g (70%) of 3-cyano-6,12-dimethyl-1,2,3,4,5,6-hexahydro-2,6-methano-9H-pyrrolo[3,2-h][3]benzazocine, which was combined with 0.39 g of the product from a previous reaction.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 2.6 hr, under nitrogen
  3. customthe layers were separated
  4. washThe organic layer was washed with sodium bicarbonate solution
  5. extractionThe combined aqueous layers were back extracted with ether
  6. washthe combined organic layers were washed with brine
  7. dry with materialdried over anhydrous potassium carbonate
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated
  10. customThe residue was purified by flash chromatography (silica gel, 2% triethylamine/ether)

Sources & evidence

ORD record
ord-3cd573ff0ff24bcca915def75e0a5a10
Source dataset
uspto-grants-1991_08
Patent number
US05037985

Reaction notes

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