Cyanogen Bromide → HCID 54260071, compound

HRID 487104Notes

Reaction equation

HRID 487104 reaction equation
C[N:2]1[CH2:11][CH2:10][C@@H:9]2[C@H:4]([CH2:5][CH2:6][C:7]3[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=32)[CH2:3]1.N#CBr>C(Cl)(Cl)Cl>[CH2:10]1[C@@H:9]2[C@H:4]([CH2:5][CH2:6][C:7]3[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=32)[CH2:3][NH:2][CH2:11]1

Participants

4

Reactant 2

HCID 10476Cyanogen BromideHCID 53876213HCID 53876213, compound

Product 1

HCID 54260071HCID 54260071, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of 0.218 g (1.08 mmol) of trans-1,2,3,4,4a,5,6,10b-octahydro-3-methyl-benz[f]isoquinoline in 3 ml of chloroform was added over 25 min to a solution of 0.140 g (1.32 mmol) of cyanogen bromide in 1 ml of chloroform under nitrogen whilst stirring magnetically. After completion of the addition, the reaction was heated to reflux for 75 min, then allowed to cool. The solvent was evaporated in vacuo, then 5 ml of 2M hydrogen chloride solution was added and the reaction was heated to reflux for 6 h, whilst stirring magnetically. After allowing to cool, the reaction mixture was made alkaline with 2M sodium hydroxide solution and extracted with ether (3×30 ml). The combined ether extracts were dried (K2CO3) and evaporated in vacuo to leave 0.186 g (92%) of the title product as a whitish solid. NMR δ(CDCl3) 1.35-1.56 (3H, m), 1.74-1.82 (1H, m), 2.35-2.50 (3H, m), 2.78-2.92 (3H, m), 3.11 (1H, m), 3.27 (1H, m), 7.06-7.17 (3H, m), 7.24 (1H, d).

Workup

  1. additionAfter completion of the addition
  2. temperaturethe reaction was heated
  3. temperatureto reflux for 75 min
  4. temperatureto cool
  5. customThe solvent was evaporated in vacuo
  6. addition5 ml of 2M hydrogen chloride solution was added
  7. temperaturethe reaction was heated
  8. temperatureto reflux for 6 h
  9. stirringwhilst stirring magnetically
  10. temperatureto cool
  11. extractionextracted with ether (3×30 ml)
  12. dry with materialThe combined ether extracts were dried (K2CO3)
  13. customevaporated in vacuo

Sources & evidence

ORD record
ord-0ee0b899a8d041a19c02019935f67b72
Source dataset
uspto-grants-1994_03
Patent number
US05294618

Reaction notes

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