Water → Desvenlafaxine

HRID 1726442Notes

Reaction equation

HRID 1726442 reaction equation
O.[S-2].[Na+].[Na+].[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.O>CN1CCCC1=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

6

Reactant 4

HCID 962WaterHCID 5656VenlafaxineHCID 8857Ethyl AcetateHCID 19906495Sodium sulfide monohydrate

Product 1

HCID 125017DesvenlafaxineYield 75.2%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent2×

Conditions

Temperature
145 °C

Procedure

A mixture of 5.7 g of sodium sulfide hydrate, and 6 mL of 1-methylpyrrolidone was heated to 145° C. under nitrogen, and then 3.5 g of venlafaxine dissolved in 6 mL of 1-methylpyrrolidone was added. The mixture was stirred and heated at 145° C. under nitrogen, approx. 3.5 g of liquid was distilled off. Reaction mixture was heated at 145° C. for 30 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 after 2 hours crystals were filtered and dried to give 2.5 g of desvenlafaxine.

Workup

  1. additionwas added
  2. temperatureheated at 145° C. under nitrogen
  3. distillationapprox. 3.5 g of liquid was distilled off
  4. customReaction mixture
  5. temperaturewas heated at 145° C. for 30 hours
  6. temperatureit was cooled
  7. filtrationcrystals were filtered
  8. customdried

Sources & evidence

ORD record
ord-c86dfc3057e74f21b9cb3fcb13113105
Source dataset
uspto-grants-2009_02
Patent number
US07491848B2

Reaction notes

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