Sodium Bicarbonate → 5-HYDROXYFLECAINIDE

HRID 1759256Notes

Reaction equation

HRID 1759256 reaction equation
[H][H].C(O)(=O)C.[OH:7][C:8]1[CH:9]=[CH:10][C:11]([O:24][CH2:25][C:26]([F:29])([F:28])[F:27])=[C:12]([CH:23]=1)[C:13]([NH:15][CH2:16][CH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][NH:18]1)=[O:14].C(=O)(O)[O-].[Na+]>C(O)(=O)C.O.[Pt]=O>[OH:7][C:8]1[CH:9]=[CH:10][C:11]([O:24][CH2:25][C:26]([F:29])([F:27])[F:28])=[C:12]([CH:23]=1)[C:13]([NH:15][CH2:16][CH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][NH:18]1)=[O:14]

Participants

7

Reactant 3

HCID 516892Sodium BicarbonateHCID 70515245HCID 70515245, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 1342955-HYDROXYFLECAINIDE

Reagents, catalysts & solvents 3

HCID 82844Platinum oxide (PtO)CatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

The crude product from Example 6 is mixed with 0.3 g of platinum oxide in 250 ml of glacial acetic acid. The mixture is reduced with hydrogen gas in a Parr apparatus. The catalyst is removed by filtration and the filtrate is evaporated to provide a solid residue. This product, 5-hydroxy-N-(2-piperidylmethyl)-2-(2,2,2-trifluoroethoxy)benzamide acetate, is dissolved in water and the aqueous solution is basified with sodium bicarbonate solution. The water solution is then extracted with a large volume of dichloromethane and the dichloromethane extracts are dried over magnesium sulfate. The magnesium sulfate is removed by filtration and the solvent is evaporated to provide a solid product. The product is recrystallized from toluene, treated with charcoal, filtered and rinsed with a toluenehexane mixture. Another recrystallization from a 1:1 mixture of toluene and hexane provides tan needles of 5-hydroxy-2-(2,2,2-trifluoroethoxy)-N-(2-piperidylmethyl)benzamide, m.p. 134°-137° C.

Workup

  1. customThe catalyst is removed by filtration
  2. customthe filtrate is evaporated
  3. customto provide a solid residue
  4. extractionThe water solution is then extracted with a large volume of dichloromethane
  5. dry with materialthe dichloromethane extracts are dried over magnesium sulfate
  6. customThe magnesium sulfate is removed by filtration
  7. customthe solvent is evaporated
  8. customto provide a solid product
  9. customThe product is recrystallized from toluene
  10. additiontreated with charcoal
  11. filtrationfiltered
  12. washrinsed with a toluenehexane mixture
  13. customAnother recrystallization
  14. additionfrom a 1:1 mixture of toluene and hexane

Sources & evidence

ORD record
ord-386f04d612e940be81e4a1077b903743
Source dataset
uspto-grants-1982_07
Patent number
US04339587

Reaction notes

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