Potassium Hydroxide → 4-(5-Fluoro-2-benzofuranyl)piperidine

HRID 2057429Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2057429
C(OC([N:6]1[CH2:11][CH2:10][CH:9]([C:12]2[O:13][C:14]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:15]=3[CH:16]=2)[CH2:8][CH2:7]1)=O)C.[OH-].[K+]>C(O)CO.C1(C)C=CC=CC=1>[F:21][C:18]1[CH:19]=[CH:20][C:14]2[O:13][C:12]([CH:9]3[CH2:8][CH2:7][NH:6][CH2:11][CH2:10]3)=[CH:16][C:15]=2[CH:17]=1

Komponenten

5

Edukt 2

HCID 14797Potassium HydroxideHCID 53928071HCID 53928071, Verbindung

Produkt 1

HCID 233123124-(5-Fluoro-2-benzofuranyl)piperidine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 174Ethylene GlycolLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

5.9 g (about 0.02 mole) of 4-(5-fluoro-2-benzofuranyl)-1-piperidinecarboxylic acid ethyl ester is dissolved in 65 ml of ethylene glycol. After the addition of 19.4 g of 86% potassium hydroxide, the cloudy solution formed is heated, with vigorous stirring, for 18 hours at 160°. The reaction solution is thereupon cooled to 100°, diluted with 65 ml of toluene and then cooled to 20°. The organic phases are firstly extracted twice with one liter of water each time, then four times with 200 ml of a 10% solution of methane sulphonic acid in water. The methanesulphonic acid solution is thereupon brought to the pH-value of 12 by the addition of 30% sodium hydroxide solution, and is subsequently extracted with one liter of chloroform. The chloroform solution is dried with sodium sulphate, filtered and concentrated by evaporation to thus obtain crude 4-(5-fluoro-2-benzofuranyl)-piperidine. The base is distilled by molecular distillation in high vacuum. The fraction distilling at 190°-200° and 0.05 Torr is 4-(5-fluoro-2-benzofuranyl)-piperidine. The hydrochloride is prepared with hydrogen chloride in ethyl acetate and recrystallised from ethyl acetate, whereupon it melts at 235°-237°.

Aufarbeitung

  1. customthe cloudy solution formed
  2. temperatureis heated, with vigorous stirring, for 18 hours at 160°
  3. temperatureThe reaction solution is thereupon cooled to 100°
  4. temperaturecooled to 20°
  5. extractionThe organic phases are firstly extracted twice with one liter of water each time
  6. additionThe methanesulphonic acid solution is thereupon brought to the pH-value of 12 by the addition of 30% sodium hydroxide solution
  7. extractionis subsequently extracted with one liter of chloroform
  8. dry with materialThe chloroform solution is dried with sodium sulphate
  9. filtrationfiltered
  10. concentrationconcentrated by evaporation

Quellen und Nachweise

ORD-Eintrag
ord-a0c0e4efc8f040689ca38c809cfb7c3f
Quelldatensatz
uspto-grants-1980_07
Patentnummer
US04210655

Notizen zur Reaktion

Wird geladen…