Formaldehyde → 1-Methyl-4-(2,3,4,5,6-pentafluorophenoxy)-4-phenylpiperidine

HRID 1031546

Reaktionsgleichung

Reaktionsgleichung von HRID 1031546
[F:1][C:2]1[C:20]([F:21])=[C:19]([F:22])[C:18]([F:23])=[C:17]([F:24])[C:3]=1[O:4][C:5]1([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1.[CH2:25]=O.[BH4-].[Na+]>CO>[CH3:25][N:8]1[CH2:7][CH2:6][C:5]([O:4][C:3]2[C:17]([F:24])=[C:18]([F:23])[C:19]([F:22])=[C:20]([F:21])[C:2]=2[F:1])([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:10][CH2:9]1

Komponenten

5

Edukt 3

HCID 712FormaldehydeHCID 4311764Sodium borohydrideHCID 146499784-(2,3,4,5,6-Pentafluorophenoxy)-4-phenylpiperidine

Produkt 1

HCID 148370691-Methyl-4-(2,3,4,5,6-pentafluorophenoxy)-4-phenylpiperidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To 50 ml of methanol, was added 4.0 g of 4-(2,3,4,5,6-pentafluorophenoxy)-4-phenylpiperidine and 15 ml of a 37% aqueous formaldehyde solution. After stirring at 70° C. for two hours, the mixture was cooled, and treated (portionwise) with 2.5 g of sodium borohydride over a period of five minutes. After stirring at ambient temperature for two hours, the reaction mixture was evaporated to a semi-solid. The semi-solid was stirred with 50 ml water, then extracted with ethyl acetate. The organic layer was washed with water, followed by a saturated sodium chloride solution, and dried over anhydrous magnesium sulfate. After filtering, evaporation of the solvent yielded a residue which was purified by means of a high pressure liquid chromatography (silica gel, elution with 5% methanol/dichloromethane). The desired fractions were combined, then evaporated to afford 1-methyl-4-(2,3,4,5,6-pentafluorophenoxy)-4-phenylpiperidine as an oil. The oil was dissolved in isopropanol, and acidified to pH 1with etheral-oxalic acid. The resultant precipitate was collected and dried to give 2.5 g (47%), of 1-methyl-4-(2,3,4,5,6-pentaflurophenoxy)-4-phenylpiperidine oxalate, m.p. 152°-154° C. (dec).

Aufarbeitung

  1. temperaturethe mixture was cooled
  2. stirringAfter stirring at ambient temperature for two hours
  3. customthe reaction mixture was evaporated to a semi-solid
  4. stirringThe semi-solid was stirred with 50 ml water
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationAfter filtering
  9. customevaporation of the solvent
  10. customyielded a residue which
  11. customwas purified by means of a high pressure liquid chromatography (silica gel, elution with 5% methanol/dichloromethane)
  12. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-054336c59c37439faf5d9e82fc6e02d5
Quelldatensatz
uspto-grants-1990_09
Patentnummer
US04954511

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