Cyanogen Bromide → HCID 53643109, compound

HRID 1885736Notes

Reaction equation

HRID 1885736 reaction equation
[N:1]#[C:2]Br.[Cl:4][C:5]1[CH2:6][N:7]=[CH:8][C:9]2([CH3:23])[CH:20]([CH3:21])[CH:18]3[CH2:19][C:13]4=[C:14]([N:17]3C)[CH2:15][CH2:16][C:10]2=[C:11]4[CH:12]=1.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[Cl:4][C:5]1[CH2:6][N:7]=[CH:8][C:9]2([CH3:23])[CH:20]([CH3:21])[CH:18]3[CH2:19][C:13]4=[C:14]([N:17]3[C:2]#[N:1])[CH2:15][CH2:16][C:10]2=[C:11]4[CH:12]=1

Participants

5

Reactant 3

HCID 10476Cyanogen BromideHCID 516892Sodium BicarbonateHCID 53780973HCID 53780973, compound

Product 1

HCID 53643109HCID 53643109, compoundYield 162.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a stirred solution of 1.68 g of cyanogen bromide and 35 ml of chloroform was added, at room temperature with stirring under nitrogen, a solution of 3.8 g of 10-chloro-1,2,3,4,5,6-hexahydro-3,6,12-trimethyl-2,6-methano-9H-pyrrolo[3,2-h][3]benzazocine and 100 ml of chloroform. The mixture was heated at reflux for 2 hr, under nitrogen, and cooled to room temperature. Dilute aqueous sodium bicarbonate solution was added and the layers separated. The organic layer was extracted with dilute aqueous sodium bicarbonate solution. The combined aqueous layers were extracted with ether and the combined organic layers were washed with brine, dried over anhydrous potassium carbonate and filtered. The filtrate was concentrated and the residue was purified by flash column chromatography (silica gel, 2% triethylamine/ethyl acetate) to afford 6.41 g (78%) of 10-chloro-3-cyano-6,12-dimethyl-1,2,3,4,5,6-hexahydro-2,6-methano-9H-pyrrolo-[3,2-h][3]benzazocine.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 2 hr, under nitrogen
  3. customthe layers separated
  4. extractionThe organic layer was extracted with dilute aqueous sodium bicarbonate solution
  5. extractionThe combined aqueous layers were 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 column chromatography (silica gel, 2% triethylamine/ethyl acetate)

Sources & evidence

ORD record
ord-a6da75b1cfa644238fa5f2ef19f01833
Source dataset
uspto-grants-1992_09
Patent number
US05145965

Reaction notes

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