Cyanogen Bromide → HCID 86737790, compound

HRID 1680236Notes

Reaction equation

HRID 1680236 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[CH2:7][C@H:8]3[N:19]([CH3:20])[CH2:18][CH2:17][C@@:14]4([C:15]=2[CH:16]=1)[C@@:9]3([O:23][CH3:24])[C@@H:10]([CH3:22])[CH2:11][C:12](=[O:21])[CH2:13]4.[N:25]#CBr.C(=O)([O-])[O-].[K+].[K+]>>[C:20]([N:19]1[CH2:18][CH2:17][C@@:14]23[C:15]4[CH:16]=[C:3]([O:2][CH3:1])[CH:4]=[CH:5][C:6]=4[CH2:7][C@@H:8]1[C@:9]2([O:23][CH3:24])[C@@H:10]([CH3:22])[CH2:11][C:12](=[O:21])[CH2:13]3)#[N:25]

Participants

4

Reactant 3

HCID 10476Cyanogen BromideHCID 11430Potassium CarbonateHCID 70569826HCID 70569826, compound

Product 1

HCID 86737790HCID 86737790, compound

Procedure

A slurry of 3,14-dimethoxy-8β,17-dimethylmorphinan-6-one (35) (4.4 g, 0.0134 mol), cyanogen bromide (4.2 g, 0.04 mol), and anhydrous potassium carbonate (5.5 g, 0.04 mol) in 140 ml of methylene chlordie was heated at reflux temperature for 22 hours under a nitrogen atmosphere. The potassium carbonate was removed by suction filtration and the filter cake washed throughly with methylene chloride. The solvent was removed from the filtrate under reduced pressure to leave 4.1 g (90% theory) of the title compound which was used in the next reaction step without further purification.

Workup

  1. temperatureat reflux temperature for 22 hours under a nitrogen atmosphere
  2. customThe potassium carbonate was removed by suction filtration
  3. washthe filter cake washed throughly with methylene chloride
  4. customThe solvent was removed from the filtrate under reduced pressure

Sources & evidence

ORD record
ord-0bc7f2991fae43948b71df65ef4694ec
Source dataset
uspto-grants-1981_06
Patent number
US04272540

Reaction notes

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