Venlafaxine → Desvenlafaxine

HRID 1838489Notes

Reaction equation

HRID 1838489 reaction equation
C(S)CCCCCCCCCCC.[CH3:14][N:15]([CH2:17][CH:18]([C:27]1([OH:33])[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1)[C:19]1[CH:20]=[CH:21][C:22]([O:25]C)=[CH:23][CH:24]=1)[CH3:16].C([O-])C.[Na+]>>[CH3:14][N:15]([CH2:17][CH:18]([C:27]1([OH:33])[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1)[C:19]1[CH:20]=[CH:21][C:22]([OH:25])=[CH:23][CH:24]=1)[CH3:16]

Participants

4

Reactant 3

HCID 5656VenlafaxineHCID 81951-DodecanethiolHCID 2723922Sodium ethoxide

Product 1

HCID 125017Desvenlafaxine

Conditions

Temperature
150 °C

Procedure

Dodecanethiol (69 g), venlafaxine (55 g), and an ethanolic solution of sodium ethanolate (21%, 82 g) are charged to a pressure vessel. The temperature is raised to 150° C. and the reaction mixture is stirred for 2 days. Then the temperature is lowered and the solution is filtered. The pH of the filtrate is adjusted to 9.5 with aqueous hydrogen chloride. The crystals are collected by suction filtration. The cake is washed with ethanol and dried in vacuo.

Workup

  1. filtrationthe solution is filtered
  2. filtrationThe crystals are collected by suction filtration
  3. washThe cake is washed with ethanol
  4. customdried in vacuo

Sources & evidence

ORD record
ord-990c11b03768404b9f1cfc8bbcf727ef
Source dataset
uspto-grants-2004_01
Patent number
US06673838B2

Reaction notes

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