Hydrochloric Acid → Venlafaxine Hydrochloride

HRID 20621

Reaction equation

HRID 20621 reaction equation
[CH3:1][N:2]([CH2:4][CH:5]([C:14]1([OH:20])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)[C:6]1[CH:7]=[CH:8][C:9]([O:12][CH3:13])=[CH:10][CH:11]=1)[CH3:3].C(OC(C)C)(=O)C.[ClH:28]>>[CH3:1][N:2]([CH2:4][CH:5]([C:14]1([OH:20])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)[C:6]1[CH:7]=[CH:8][C:9]([O:12][CH3:13])=[CH:10][CH:11]=1)[CH3:3].[ClH:28]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 5656VenlafaxineHCID 7915Isopropyl Acetate

Product 1

HCID 62923Venlafaxine HydrochlorideYield 88%

Procedure

To the solution of venlafaxine base in isopropyl acetate from example 1 (66 ml, 10 mmol) 5 ml of 2 M aqueous HCl were added. The mixture was heated and water was removed by azeotropic distillation using a Dean-Starck trap. When all water was removed from the mixture, the product began slowly to crystallize. The obtained suspension was heated under reflux temperature for 1.5 h, then cooled and filtered. 2.75 g (88% from N,N-didesmethyl venlafaxine hydrochloride) of pure venlafaxine hydrochloride form I (HPLC: 99.65 area %) were obtained.

Workup

  1. temperatureThe mixture was heated
  2. customwater was removed by azeotropic distillation
  3. customWhen all water was removed from the mixture
  4. customto crystallize
  5. temperatureThe obtained suspension was heated
  6. temperatureunder reflux temperature for 1.5 h
  7. temperaturecooled
  8. filtrationfiltered

Sources & evidence

ORD record
ord-b19b7219e7da48a7bfb6ddb406b91cc9
Source dataset
uspto-grants-2010_06
Patent number
US07745664B2

Linked notes

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