4-Hydroxybenzyl Alcohol → 4-[[4-(2-Methoxyphenyl)piperazin-1-yl]methyl]phenol

HRID 847435

Reaktionsgleichung

Reaktionsgleichung von HRID 847435
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]O)=[CH:4][CH:3]=1.[CH3:10][O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[N:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1.[OH-].[K+].[Br-].[Li+]>C1(C)C=CC=CC=1.O>[CH3:10][O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[N:18]1[CH2:23][CH2:22][N:21]([CH2:8][C:5]2[CH:4]=[CH:3][C:2]([OH:1])=[CH:7][CH:6]=2)[CH2:20][CH2:19]1

Komponenten

7

Edukt 4

HCID 1254-Hydroxybenzyl AlcoholHCID 13461-(2-Methoxyphenyl)piperazineHCID 14797Potassium HydroxideHCID 82050Lithium Bromide

Produkt 1

HCID 13771494-[[4-(2-Methoxyphenyl)piperazin-1-yl]methyl]phenolAusbeute 56 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

4-Hydroxyphenyl methanol (124 g, 1 mole) and 192 g (1 mole) of 1-(2-methoxyphenyl)piperazine, together with 56 g (1 mole) of potassium hydroxide and 8.7 g (0.1 mole) of lithium bromide and 32.2 g (0.1 mole) of Aliquat 366 were dissolved in a mixture of 1 liter of toluene and 1 liter of water. The reaction mixture was refluxed for 24 hours, and then allowed to cool to room temperature. The organic layer was decanted and extracted twice with 500 ml of a 10% sodium hydroxide solution. The basic aqueous liquor was treated with ammonium acetate to provoke precipitation of the desired product. After filtration and drying under vacuum overnight at 50° C., 167 g (0.56 mole, 56% yield) of the title product was obtained as small white leaflets melting at 172° C.

Aufarbeitung

  1. temperatureThe reaction mixture was refluxed for 24 hours
  2. customThe organic layer was decanted
  3. extractionextracted twice with 500 ml of a 10% sodium hydroxide solution
  4. additionThe basic aqueous liquor was treated with ammonium acetate
  5. customprecipitation of the desired product
  6. filtrationAfter filtration
  7. customdrying under vacuum overnight at 50° C.

Quellen und Nachweise

ORD-Eintrag
ord-0ebeb5b64dfb451d93a06df6381c57ed
Quelldatensatz
uspto-grants-1992_08
Patentnummer
US05142052

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