Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetone | HCID 180 | — |
| Reactant | Water | HCID 962 | — |
| Reactant | Venlafaxine | HCID 5656 | — |
| Reactant | Sodium Cyanide | HCID 8929 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Product | Desvenlafaxine | HCID 125017 | — |
Reaction Steps
5.0 g Venlafaxine was dissolved in 50 ml dimethylsulfoxide at 25-30° C. Sodium cyanide 9.0 g was added and reaction mass was heated to 180-185° C. for 4 hours. The reaction mass was cooled and 25 ml water was added. The resulting solution was extracted with 2×50 ml ethyl acetate, combined organic layer was dried over anhydrous sodium sulfate, followed by distillation to give residue. The residue was treated with 25 ml acetone then cooled to 0-5° C. to give O-desmethylvenlafaxine.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08329952B2 |
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| Source dataset | uspto-grants-2012_12 |
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| ORD ID | ord-30767d15745245cea4be0047329c469d |
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| Source note | uspto-grants-2012_12 |
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