Water → Flecainide

HRID 460428Notes

Reaction equation

HRID 460428 reaction equation
[F:1][C:2]([F:22])([F:21])[CH2:3][O:4][C:5]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]([F:20])([F:19])[F:18])=[CH:11][C:6]=1[C:7]([O:9]C)=O.[NH2:23][CH2:24][CH:25]1[CH2:30][CH2:29][CH2:28][CH2:27][NH:26]1.O>C1(C)C=CC=CC=1>[CH:13]1[C:12]([O:15][CH2:16][C:17]([F:20])([F:19])[F:18])=[CH:11][C:6]([C:7]([NH:23][CH2:24][CH:25]2[NH:26][CH2:27][CH2:28][CH2:29][CH2:30]2)=[O:9])=[C:5]([O:4][CH2:3][C:2]([F:1])([F:22])[F:21])[CH:14]=1

Participants

5

Reactant 3

HCID 962WaterHCID 90865Piperidine-2-methylamineHCID 2727094Methyl 2,5-bis(2,2,2-trifluoroethoxy)benzoate

Product 1

HCID 3356FlecainideYield 87.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of methyl 2,5-bis(2,2,2-trifluoroethoxy)benzoate (1.5 g), 2-(aminomethyl)piperidine (0.62 g) in toluene (3 ml) was stirred at reflux for 10 hours. After cooling to room temperature, water (10 ml) was added and two layers solution were separated. The aqueous layer was extracted with toluene (2×10 ml) and the combined organic layers were washed with water (3×10 ml). The organic layer was concentrated under reduced pressure to give Flecainide free base as a white solid (1.63 g, 85%).

Workup

  1. temperatureat reflux for 10 hours
  2. customtwo layers solution were separated
  3. extractionThe aqueous layer was extracted with toluene (2×10 ml)
  4. washthe combined organic layers were washed with water (3×10 ml)
  5. concentrationThe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-da87f08ae68749968e27a5d0ae886fab
Source dataset
uspto-grants-2007_03
Patent number
US07196197B2

Reaction notes

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