Venlafaxine → Desvenlafaxine

HRID 1726444Notes

Reaction equation

HRID 1726444 reaction equation
[S-2].[Na+].[Na+].CN1CCCC1=O.[CH3:11][N:12]([CH2:14][CH:15]([C:24]1([OH:30])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1)[C:16]1[CH:17]=[CH:18][C:19]([O:22]C)=[CH:20][CH:21]=1)[CH3:13].C(OC(=O)C)C>O>[CH3:11][N:12]([CH2:14][CH:15]([C:24]1([OH:30])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1)[C:16]1[CH:17]=[CH:18][C:19]([OH:22])=[CH:20][CH:21]=1)[CH3:13]

Participants

6

Reactant 4

HCID 5656VenlafaxineHCID 8857Ethyl AcetateHCID 13387N-methyl-2-pyrrolidoneHCID 14804Sodium Sulfide

Product 1

HCID 125017DesvenlafaxineYield 77.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
145 °C

Procedure

A mixture of 78.5 g of anhydrous sodium sulfide, and 525 mL of 1-methylpyrrolidone was heated to 145° C. under nitrogen, and then 145 g of venlafaxine was added. The mixture was stirred and heated at 145° C. under nitrogen for 30 hours, then it was cooled and mixed with 2.9 L of ethylacetate and 2.0 L of water. The mixture was kept in the refrigerator overnight, crystals were filtered and dried to give 106.5 g of desvenlafaxine. Yield 77%.

Workup

  1. temperatureheated at 145° C. under nitrogen for 30 hours
  2. temperatureit was cooled
  3. customwas kept in the refrigerator overnight, crystals
  4. filtrationwere filtered
  5. customdried

Sources & evidence

ORD record
ord-acc399af111e4fa9b654b8bd354a44e1
Source dataset
uspto-grants-2009_02
Patent number
US07491848B2

Reaction notes

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