Cyanogen Bromide → HCID 86737291, compound

HRID 904206Notes

Reaction equation

HRID 904206 reaction equation
[CH3:1][C@@H:2]1[C@@H:15]2[C@:6]3([CH2:18][CH2:17][N:16]([CH3:19])[C@@H:14]2[CH2:13][C:12]2[CH:11]=[CH:10][C:9]([O:20][CH3:21])=[CH:8][C:7]3=2)[CH2:5][C:4](=[O:22])[CH2:3]1.C([O-])([O-])=O.[K+].[K+].[N:29]#CBr>C(Cl)(Cl)Cl>[C:19]([N:16]1[CH2:17][CH2:18][C@@:6]23[C:7]4[CH:8]=[C:9]([O:20][CH3:21])[CH:10]=[CH:11][C:12]=4[CH2:13][C@@H:14]1[C@@H:15]2[C@@H:2]([CH3:1])[CH2:3][C:4](=[O:22])[CH2:5]3)#[N:29]

Participants

5

Reactant 3

HCID 10476Cyanogen BromideHCID 11430Potassium CarbonateHCID 53821342HCID 53821342, compound

Product 1

HCID 86737291HCID 86737291, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A rapidly stirred mixture of 8β,17-dimethyl-3-methoxymorphinan-6-one (free base; prepared in Part A) in chloroform (1.0 g/10 ml) containing 1.5 g finely powdered dry K2CO3 was treated dropwise with a solution of cyanogen bromide in chloroform (1.2 equivalents; 1.0 g/20 ml). The mixture was stirred rapidly for 30 minutes and then heated at reflux for an additional two hours. The solution was cooled, filtered, evaporated to dryness and azeotroped with alcohol. The crystalline, mp. 202°-205° C., product was obtained in 81% yield and was used without further pruification.

Workup

  1. additioncontaining 1.5 g
  2. temperatureheated
  3. temperatureat reflux for an additional two hours
  4. temperatureThe solution was cooled
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customazeotroped with alcohol
  8. customThe crystalline, mp. 202°-205° C., product was obtained in 81% yield

Sources & evidence

ORD record
ord-d1a11f756e3845039c765c53ab3cc980
Source dataset
uspto-grants-1980_10
Patent number
US04230712

Reaction notes

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