Venlafaxine → Desvenlafaxine

HRID 860913

Reaction equation

HRID 860913 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-].[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 10942334Sodium Methoxide

Product 1

HCID 125017Desvenlafaxine

Conditions

Temperature
190 °C

Procedure

Dodecanethiol (122 g), venlafaxine (111 g), and a methanolic solution of sodium methanolate (30%, 90 g) and PEG 400 are heated to 190° C. The methanol is distilled off and the solution is stirred for 2 hours at 190° C. Then the temperature is lowered, 2-propanol (450 g) is added and the pH is adjusted to 9.5 with aqueous HCl. The precipitate is collected by suction filtration, and the cake is washed with 2-propanol, toluene, 2-propanol and water. The wet O-desmethylvenlafaxine is dried in vacuo.

Workup

  1. distillationThe methanol is distilled off
  2. addition2-propanol (450 g) is added
  3. filtrationThe precipitate is collected by suction filtration
  4. washthe cake is washed with 2-propanol, toluene, 2-propanol and water
  5. dry with materialThe wet O-desmethylvenlafaxine is dried in vacuo

Sources & evidence

ORD record
ord-014df8edd2784c42bdd24c0f8e68eb7e
Source dataset
uspto-grants-2006_12
Patent number
US07154001B2

Linked notes

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