Hydrochloric Acid → HCID 22870688, compound

HRID 976091Notes

Reaction equation

HRID 976091 reaction equation
[OH2:1].[CH:2]1[C:18]2[CH2:17][C@H:16]3[N:19]([CH2:21][CH2:22][C@@:8]45[C@H:15]3[CH:14]=[CH:13][C@H:11]([OH:12])[C@@H:9]4[O:10][C:6]([C:7]=25)=[C:4]([OH:5])[CH:3]=1)[CH3:20].[H-].[K+].[CH2:25](I)[CH3:26].Cl>O1CCCC1.O>[CH2:25]([O:1][O:12][C@H:11]1[CH:13]=[CH:14][C@@H:15]2[C@:8]34[CH2:22][CH2:21][N:19]([CH3:20])[C@@H:16]2[CH2:17][C:18]2[CH:2]=[CH:3][C:4]([OH:5])=[C:6]([O:10][C@@H:9]13)[C:7]4=2)[CH3:26]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6340IodoethaneHCID 82127Potassium hydrideHCID 211186826009-81-0

Product 1

HCID 22870688HCID 22870688, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Morphine hydrate (1.42 g, 4.68×10-3 mol) in anhydrous tetrahydrofuran (50 ml) was added dropwise over 20 min. to a stirring suspension, under argon and on an ice/water bath, of potassium hydride (1.75 g, 4.36×10-2 mol) in anhydrous tetrahydrofuran (50 ml). The suspension was stirred for 6 h. under argon on an ice/water bath and then the suspension was allowed to warm to room temperature. Ethyl iodide (0.72 ml, 9×10-3 mol) was added and the suspension was stirred under argon at room temperature for 1 h. The suspension was cooled on an ice/water bath and water (10 ml) was added dropwise to the suspension followed by hydrochloric acid (1N, 50 ml). The solvents were removed in vacuo, water (50 ml) was added to the residue and the suspension was filtered. The aqueous filtrate was extracted 2 times with chloroform (40 ml). The aqueous phase was then treated with hydrochlorid acid (6N, 5 ml) to achieve a pH of 7. The aqueous phase was then extracted 10 times with chloroform (400 ml). The combined chloroform phases were dried over magnesium sulfate, filtered and the solvent was removed in vacuo. The title compound was recovered (430 mg) as a pale brown glassy solid.

Workup

  1. stirringthe suspension was stirred under argon at room temperature for 1 h
  2. temperatureThe suspension was cooled on an ice/water bath
  3. customThe solvents were removed in vacuo, water (50 ml)
  4. additionwas added to the residue
  5. filtrationthe suspension was filtered
  6. extractionThe aqueous filtrate was extracted 2 times with chloroform (40 ml)
  7. additionThe aqueous phase was then treated with hydrochlorid acid (6N, 5 ml)
  8. extractionThe aqueous phase was then extracted 10 times with chloroform (400 ml)
  9. dry with materialThe combined chloroform phases were dried over magnesium sulfate
  10. filtrationfiltered
  11. customthe solvent was removed in vacuo
  12. customThe title compound was recovered (430 mg) as a pale brown glassy solid

Sources & evidence

ORD record
ord-4b46c14702364b8e9e2df50ccc70c794
Source dataset
uspto-grants-1997_03
Patent number
US05610283

Reaction notes

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