Sodium Hydroxide → spiro(9H-fluorene-9,3'-piperidine)-2'-one

HRID 1153877Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1153877
[C:1]([C:4]1([CH2:17][CH2:18][CH2:19]N)[C:16]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:10]2[C:5]1=[CH:6][CH:7]=[CH:8][CH:9]=2)(=[O:3])[NH2:2].[OH-].[Na+]>CO.Cl>[NH:2]1[CH2:19][CH2:18][CH2:17][C:4]2([C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[C:10]3[C:5]2=[CH:6][CH:7]=[CH:8][CH:9]=3)[C:1]1=[O:3]

Komponenten

5

Edukt 2

HCID 14798Sodium HydroxideHCID 127612Deisopropylindecainide

Produkt 1

HCID 13368046spiro(9H-fluorene-9,3'-piperidine)-2'-oneAusbeute 72,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittel2×HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A solution of 5.0 g (18.8 mM) of 9-carbamoyl-9-(3-aminopropyl)fluorene (prepared as described in U.S. Pat. No. 4,282,170) in 50 ml of methanol saturated with hydrogen chloride was heated at reflux for sixteen hours. The reaction mixture was cooled and concentrated to dryness to give a solid. The solid was dissolved in 1N hydrochloric acid and the solution was heated to 100° C. for five minutes. The acidic mixture was diluted by addition of 50% aqueous sodium hydroxide to pH 10. The aqueous alkaline solution was extracted several times with chloroform, and the extracts were combined, washed with water and with brine and dried. Removal of the solvent by evaporation under reduced pressure provided a solid that was crystallized from dichloromethane and petroleum ether to afford 3.4 g of spiro(9H-fluorene-9,3'-piperidine)-2'-one. m.p. >250° C.

Aufarbeitung

  1. temperatureat reflux for sixteen hours
  2. temperatureThe reaction mixture was cooled
  3. concentrationconcentrated to dryness
  4. customto give a solid
  5. extractionThe aqueous alkaline solution was extracted several times with chloroform
  6. washwashed with water and with brine
  7. customdried
  8. customRemoval of the solvent
  9. customby evaporation under reduced pressure
  10. customprovided a solid
  11. customthat was crystallized from dichloromethane and petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-01d901a8fbd7414697848f899430b97a
Quelldatensatz
uspto-grants-1984_12
Patentnummer
US04486592

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