Hydrochloric Acid → HCID 70568077, compound

HRID 1680237Notes

Reaction equation

HRID 1680237 reaction equation
C([N:3]1[CH2:21][CH2:20][C@@:10]23[C:11]4[CH:12]=[C:13]([O:18][CH3:19])[CH:14]=[CH:15][C:16]=4[CH2:17][C@@H:4]1[C@:5]2([O:24][CH3:25])[C@@H:6]([CH3:23])[CH2:7][C:8](=[O:22])[CH2:9]3)#N.C([O-])([O-])=O.[Na+].[Na+].NC(N)=O.C(O)C.[ClH:39]>O.C(OCC)C>[ClH:39].[CH3:19][O:18][C:13]1[CH:14]=[CH:15][C:16]2[CH2:17][C@H:4]3[NH:3][CH2:21][CH2:20][C@@:10]4([C:11]=2[CH:12]=1)[C@@:5]3([O:24][CH3:25])[C@@H:6]([CH3:23])[CH2:7][C:8](=[O:22])[CH2:9]4

Participants

8

Reactant 5

HCID 313Hydrochloric Acid2×HCID 702EthanolHCID 1176UreaHCID 10340Sodium CarbonateHCID 86737790HCID 86737790, compound

Product 1

HCID 70568077HCID 70568077, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 17-cyano-3,14-dimethoxy-8β-methyl morphinan-6-one (36) (3.6 g, 0.011 mol) in 100 ml of 4 N HCl was heated at 80°-90° C. in an oil bath for 16 hours. The reaction mixture was cooled, diluted with 150 ml of H2O and made basic with Na2CO3. The aqueous solution was extracted with four portions of chloroform, dried over Na2SO4 and concentrated under reduced pressure to give 3.8 g of crude product. The NMR spectrum of this crude material indicated the presence of the intermediate urea, and the crude material was therefore dissolved in 150 ml of 4 N HCl and heated at reflux for 10 additional hours. Similar workup as described above yielded 0.4 g of crude product which was taken up in diethyl ether, and treated with ethanol to give a precipitate. Collection of the precipitate by suction filtration gave 1.38 g (36% theory) of the title compound as a tan solid which was used in the next step without further purification.

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionThe aqueous solution was extracted with four portions of chloroform
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customto give 3.8 g of crude product
  6. temperatureheated
  7. temperatureat reflux for 10 additional hours
  8. customabove yielded 0.4 g of crude product which
  9. customto give a precipitate
  10. customCollection of the precipitate
  11. filtrationby suction filtration

Sources & evidence

ORD record
ord-52f8c73fd83d4d0291dd9a7655bf527b
Source dataset
uspto-grants-1981_06
Patent number
US04272540

Reaction notes

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