Formic Acid → 1-Formyl-4-(2,3,4,5,6-pentafluorophenoxy)-4-phenylpiperidine

HRID 1721862Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1721862
[CH:1](O)=[O:2].C(OC(=O)C)(=O)C.[F:11][C:12]1[C:30]([F:31])=[C:29]([F:32])[C:28]([F:33])=[C:27]([F:34])[C:13]=1[O:14][C:15]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1.C(=O)(O)[O-].[Na+]>C(OCC)C.O>[CH:1]([N:18]1[CH2:17][CH2:16][C:15]([O:14][C:13]2[C:27]([F:34])=[C:28]([F:33])[C:29]([F:32])=[C:30]([F:31])[C:12]=2[F:11])([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:20][CH2:19]1)=[O:2]

Komponenten

7

Edukt 4

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 146499784-(2,3,4,5,6-Pentafluorophenoxy)-4-phenylpiperidine

Produkt 1

HCID 146499961-Formyl-4-(2,3,4,5,6-pentafluorophenoxy)-4-phenylpiperidineAusbeute 64 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

A mixture of 1.5 ml of formic acid and 3.5 ml of acetic anhydride was stirred at 55° C. for one hour, cooled and then treated with a solution of 4.0 g of 4-(2,3,4,5,6-pentafluorophenoxy)-4-phenylpiperidine in 50 ml of diethyl ether. After stirring at ambient temperature for three hours, the reaction mixture was poured into 100 ml of water, basified to a pH of about 10 by the addition of sodium bicarbonate, and extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, filtered and concentrated to an oil. High pressure liquid chromatography of the oil (silica gel; elution with ethyl acetate) afforded a solid which was recrystallized from isopropyl ether/hexanes (1:2) to yield 2.1 g (64%) of 1-formyl-4-(2,3,4,5,6-pentafluorophenoxy)-4-phenylpiperidine, m.p. 118°-119° C.

Aufarbeitung

  1. temperaturecooled
  2. stirringAfter stirring at ambient temperature for three hours
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to an oil
  8. washHigh pressure liquid chromatography of the oil (silica gel; elution with ethyl acetate)
  9. customafforded a solid which
  10. customwas recrystallized from isopropyl ether/hexanes (1:2)

Quellen und Nachweise

ORD-Eintrag
ord-448c01ecf29c4ea984a587a9046ee596
Quelldatensatz
uspto-grants-1989_08
Patentnummer
US04853384

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