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

HRID 1605960ノート

反応式

HRID 1605960 の反応式
[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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 23925Iron触媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-919f6738bd534276b667e98cc7e7994b
出典データセット
uspto-grants-1976_04
特許番号
US03951987

反応ノート

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