Cyanogen Bromide → HCID 57271803, compound

HRID 1680218Notes

Reaction equation

HRID 1680218 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:22][CH3:23])[CH2:10][CH2:11][C:12](=[O:21])[CH2:13]4.[N:24]#CBr.C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl>[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:22][CH3:23])[CH2:10][CH2:11][C:12](=[O:21])[CH2:13]3)#[N:24]

Participants

5

Reactant 3

HCID 10476Cyanogen BromideHCID 11430Potassium CarbonateHCID 57017342HCID 57017342, compound

Product 1

HCID 57271803HCID 57271803, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3,14-dimethoxy-17-methylmorphinan-6-one (0.490 g, 1.55 mmol) in methylene chloride (25 ml) was treated with cyanogen bromide (0.977 g, 9.3 mmol) and anhydrous potassium carbonate (1.285 g, 9.3 mmol). The mixture was refluxed for 22 hours, filtered through Celite and the filtrate washed with water (3×50 ml). The organic solution was separated, dried over MgSO4, filtered and concentrated under reduced pressure to give 0.463 g (92% theory) of the desired product as a yellow solid (m.p. 172°-176°). Recrystallization from ethanol gave 0.427 g (85% theory) of the product as a white solid, m.p. 176°-177° C.

Workup

  1. temperatureThe mixture was refluxed for 22 hours
  2. filtrationfiltered through Celite
  3. washthe filtrate washed with water (3×50 ml)
  4. customThe organic solution was separated
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5a945ce942de4805801abb91a765eb77
Source dataset
uspto-grants-1981_06
Patent number
US04272540

Reaction notes

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