Sodium Carbonate → HCID 86737313, compound

HRID 224353Notes

Reaction equation

HRID 224353 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[CH2:7][C@H:8]3[N:20]([CH3:21])[CH2:19][CH2:18][C@:14]45[C:15]=2[C:16]=1[O:17][C@H:13]4[C:12](=[O:22])[CH2:11][C@@H:10]([CH3:23])[C@@:9]35[O:24][CH3:25].C([O-])([O-])=O.[Na+].[Na+].[N:32]#CBr>C(Cl)(Cl)Cl>[C:21]([N:20]1[CH2:19][CH2:18][C@:14]23[C:15]4[C:16]5[O:17][C@H:13]2[C:12](=[O:22])[CH2:11][C@@H:10]([CH3:23])[C@@:9]3([O:24][CH3:25])[C@H:8]1[CH2:7][C:6]=4[CH:5]=[CH:4][C:3]=5[O:2][CH3:1])#[N:32]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 10476Cyanogen BromideHCID 70592537HCID 70592537, compound

Product 1

HCID 86737313HCID 86737313, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 3,14-dimethoxy-8α,17-dimethyl-4,5α-epoxymorphinan-6-one (2) (0.89 g, 2.59 mmol) in a mixture of 25 milliliters CHCl3 /25 milliliters CH2Cl2 was treated with anhydrous Na2CO3 (1.6 g, 15.09 mmol), followed by cyanogen bromide (1.6 g, 15.10 mmol). The reaction mixture was refluxed overnight with stirring while being kept under a nitrogen atmosphere. The sodium carbonate was removed by filtration and the filtrate concentrated under reduced pressure to give 0.89 g (97%) of the title compound as a brownish solid. The product, which showed only a single spot on tlc, was used without further purification.

Workup

  1. temperatureThe reaction mixture was refluxed overnight
  2. customThe sodium carbonate was removed by filtration
  3. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-7fd9f59f754f40f3929086ca28dbb388
Source dataset
uspto-grants-1980_11
Patent number
US04232028

Reaction notes

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