Acetone → Desvenlafaxine

HRID 2193972Notes

Reaction equation

HRID 2193972 reaction equation
[CH3:1][N:2]([CH2:4][CH:5]([C:14]1([OH:20])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)[C:6]1[CH:7]=[CH:8][C:9]([O:12]C)=[CH:10][CH:11]=1)[CH3:3].[C-]#N.[Na+].O.CC(C)=O>CS(C)=O>[CH3:1][N:2]([CH2:4][CH:5]([C:14]1([OH:20])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)[C:6]1[CH:7]=[CH:8][C:9]([OH:12])=[CH:10][CH:11]=1)[CH3:3]

Participants

6

Reactant 4

HCID 180AcetoneHCID 962WaterHCID 5656VenlafaxineHCID 8929Sodium Cyanide

Product 1

HCID 125017Desvenlafaxine

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
182.5 °C

Procedure

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.

Workup

  1. customreaction mass
  2. temperatureThe reaction mass was cooled
  3. extractionThe resulting solution was extracted with 2×50 ml ethyl acetate
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. distillationfollowed by distillation
  6. customto give residue
  7. temperaturethen cooled to 0-5° C.

Sources & evidence

ORD record
ord-30767d15745245cea4be0047329c469d
Source dataset
uspto-grants-2012_12
Patent number
US08329952B2

Reaction notes

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