Acetic Acid → Flecainide Acetate

HRID 460429

Reaction equation

HRID 460429 reaction equation
[CH:1]1[C:6]([O:7][CH2:8][C:9]([F:12])([F:11])[F:10])=[CH:5][C:4]([C:13]([NH:15][CH2:16][CH:17]2[NH:22][CH2:21][CH2:20][CH2:19][CH2:18]2)=[O:14])=[C:3]([O:23][CH2:24][C:25]([F:28])([F:27])[F:26])[CH:2]=1.[C:29]([OH:32])(=[O:31])[CH3:30].CCCCCC>C(O)(C)C>[CH3:30][C:29]([OH:32])=[O:31].[CH:1]1[C:6]([O:7][CH2:8][C:9]([F:12])([F:10])[F:11])=[CH:5][C:4]([C:13]([NH:15][CH2:16][CH:17]2[NH:22][CH2:21][CH2:20][CH2:19][CH2:18]2)=[O:14])=[C:3]([O:23][CH2:24][C:25]([F:27])([F:26])[F:28])[CH:2]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 3356FlecainideHCID 8058Hexane

Product 1

HCID 41022Flecainide AcetateYield 89.7%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of Flecainide free base (1.5 g) in isopropanol (7.5 ml) was added glacial acetic acid (0.3 g) and the solution was stirred under reflux for 2 hours. The solution was cooled to room temperature and hexane (15 ml) was added and solids began to precipitate. The resulting suspension was stirred at 20–25° C. for 2 hours and the solids were filtered and then rinsed with hexane (2×10 ml). The damp cake was dried in vacuum for 4 hours to give Flecainide acetate as a white solid (1.54 g, Yield 89%).

Workup

  1. temperatureunder reflux for 2 hours
  2. customto precipitate
  3. stirringThe resulting suspension was stirred at 20–25° C. for 2 hours
  4. filtrationthe solids were filtered
  5. washrinsed with hexane (2×10 ml)
  6. customThe damp cake was dried in vacuum for 4 hours

Sources & evidence

ORD record
ord-7e43a0d3462442afab3492070cd7811c
Source dataset
uspto-grants-2007_03
Patent number
US07196197B2

Linked notes

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