Acetic Acid → Flecainide Acetate

HRID 1788811

Reaktionsgleichung

Reaktionsgleichung von HRID 1788811
[F:1][C:2]([F:28])([F:27])[CH2:3][O:4][C:5]1[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:23]([F:26])([F:25])[F:24])=[CH:17][C:6]=1[C:7]([NH:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1)=[O:8].[C:29]([OH:32])(=[O:31])[CH3:30].[H][H]>[Pt].CCCCCC>[C:29]([OH:32])(=[O:31])[CH3:30].[F:28][C:2]([F:1])([F:27])[CH2:3][O:4][C:5]1[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:23]([F:26])([F:25])[F:24])=[CH:17][C:6]=1[C:7]([NH:9][CH2:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][NH:12]1)=[O:8]

Komponenten

6

Edukt 3

HCID 176Acetic AcidHCID 936692,5-Bis(2,2,2-trifluoroethoxy)-N-(2-pyridylmethyl)benzamideHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 41022Flecainide AcetateAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23939PlatinumKatalysatorHCID 8058HexaneLösungsmittel

Versuchsvorschrift

A mixture of 0.33 mole (134.7 g.) 2,5-bis(2,2,2-trifluoroethoxy)-N-(2-pyridylmethyl)benzamide, 1.347 liter of glacial acetic acid and 13.5 g. of 5 percent platinum on carbon is reduced in a Parr apparatus at a pressure of about 10 pounds of hydrogen at room temperature. The reaction is complete in 6-7 hours. The reaction mixture is filtered and the catalyst is washed with isopropyl alcohol. The solution and washings are evaporated to provide a residue. Hexane is added to the residue and the resulting white solid is collected and recrystallized from a mixture of acetone and hexane. A 71 percent yield of 2,5-bis(2,2,2-trifluoroethoxy)-N-(2-piperidylmethyl)benzamide acetate, m.p. 150° to 152° C., is obtained. By concentrating the residual liquid an additional 18 percent of product is obtained as a second crop with a melting point of 148°-150° C.

Aufarbeitung

  1. filtrationThe reaction mixture is filtered
  2. washthe catalyst is washed with isopropyl alcohol
  3. customThe solution and washings are evaporated
  4. customto provide a residue
  5. customthe resulting white solid is collected
  6. customrecrystallized from a mixture of acetone and hexane

Quellen und Nachweise

ORD-Eintrag
ord-c720cf44b01b4661bc3a257853320079
Quelldatensatz
uspto-grants-1987_08
Patentnummer
US04684733

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