Hydrochloric Acid → 1-[2-(p-Aminophenoxy)ethyl]-4-(p-fluorophenyl)-1,2,3,6-tetrahydropyridine dihydrochloride

HRID 1605960Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1605960
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:9][CH2:10][N:11]([CH2:14][CH2:15][O:16][C:17]3[CH:22]=[CH:21][C:20]([N+:23]([O-])=O)=[CH:19][CH:18]=3)[CH2:12][CH:13]=2)=[CH:4][CH:3]=1.[ClH:26].C(O)C.[OH-].[Na+]>C(OCC)(=O)C.[Fe].O>[ClH:26].[ClH:26].[NH2:23][C:20]1[CH:19]=[CH:18][C:17]([O:16][CH2:15][CH2:14][N:11]2[CH2:10][CH:9]=[C:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)[CH2:13][CH2:12]2)=[CH:22][CH:21]=1

Komponenten

8

Edukt 4

HCID 313Hydrochloric Acid3×HCID 702EthanolHCID 14798Sodium HydroxideHCID 215456084-(p-Fluorophenyl)-1,2,3,6-tetrahydro-1-[2-(p-nitrophenoxy)ethyl]pyridine

Produkt 1

HCID 215456061-[2-(p-Aminophenoxy)ethyl]-4-(p-fluorophenyl)-1,2,3,6-tetrahydropyridine dihydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23925IronKatalysatorHCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

0.2 g. of powdered iron is added to a solution of 0.34 g. of 4-(p-fluorophenyl)-1,2,3,6-tetrahydro-1-[2-(p-nitrophenoxy) ethyl]pyridine in a mixture of 2 ml. of 1N hydrochloric acid, 10 ml. of ethanol and 10 ml. of water. The mixture is refluxed for 4 hrs., cooled and made alkaline by addition of 1N sodium hydroxide. After addition of 20 ml. of chloroform and celite, the mixture is filtered. The organic phase is separated, dried and evaporated. The oily residue obtained is dissolved in ethyl acetate and converted to the hydrochloride by addition of ethanolic hydrogen chloride. The 1-[2-(p-aminophenoxy)ethyl]-4-(p-fluorophenyl)-1,2,3,6-tetrahydropyridine dihydrochloride obtained in this way has m.p. 180°-181° after recrystallization from ethanol/ethylacetate/ether.

Aufarbeitung

  1. temperatureThe mixture is refluxed for 4 hrs
  2. temperature, cooled
  3. additionAfter addition of 20 ml
  4. filtrationof chloroform and celite, the mixture is filtered
  5. customThe organic phase is separated
  6. customdried
  7. customevaporated
  8. customThe oily residue obtained

Quellen und Nachweise

ORD-Eintrag
ord-919f6738bd534276b667e98cc7e7994b
Quelldatensatz
uspto-grants-1976_04
Patentnummer
US03951987

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