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

HRID 1605960Notes

Reaction equation

HRID 1605960 reaction equation
[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

Participants

8

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-919f6738bd534276b667e98cc7e7994b
Source dataset
uspto-grants-1976_04
Patent number
US03951987

Reaction notes

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