Venlafaxine → Desvenlafaxine

HRID 1726443Notes

Reaction equation

HRID 1726443 reaction equation
[S-2].[Na+].[Na+].[Se].[CH3:5][N:6]([CH2:8][CH:9]([C:18]1([OH:24])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1)[C:10]1[CH:11]=[CH:12][C:13]([O:16]C)=[CH:14][CH:15]=1)[CH3:7].C(OC(=O)C)C>CN1CCCC1=O.O>[CH3:5][N:6]([CH2:8][CH:9]([C:18]1([OH:24])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1)[C:10]1[CH:11]=[CH:12][C:13]([OH:16])=[CH:14][CH:15]=1)[CH3:7]

Participants

7

Reactant 4

HCID 5656VenlafaxineHCID 8857Ethyl AcetateHCID 14804Sodium SulfideHCID 6326970Selenium

Product 1

HCID 125017DesvenlafaxineYield 60.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent2×

Conditions

Temperature
145 °C

Procedure

A mixture of 1.90 g of anhydrous sodium sulfide, 2.0 g of selenium and 6 mL of 1-methylpyrrolidone was heated to 145° C. under nitrogen, and then 3.5 g of venlafaxine dissolved in 10 mL of 1-methylpyrrolidone was added. The mixture was stirred and heated at 145° C. under nitrogen. Reaction mixture was heated at 145° C. for 16 hours, then it was cooled and mixed with 70 mL of ethylacetate and 50 mL of water. The mixture was placed into a refrigerator and crystals were filtered. After being recrystallized from 45 mL of ethanol, 2.0 g of desvenlafaxine was obtained with the yield 60%.

Workup

  1. additionwas added
  2. temperatureheated at 145° C. under nitrogen
  3. customReaction mixture
  4. temperaturewas heated at 145° C. for 16 hours
  5. temperatureit was cooled
  6. filtrationwere filtered
  7. customAfter being recrystallized from 45 mL of ethanol

Sources & evidence

ORD record
ord-57307f7f8f7e41c68f5e2073ae861717
Source dataset
uspto-grants-2009_02
Patent number
US07491848B2

Reaction notes

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