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

HRID 847436

Reaction equation

HRID 847436 reaction equation
[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.[Br-].[Li+].[OH-].[K+]>C1(C)C=CC=CC=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][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

Participants

6

Reactant 4

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

Product 1

HCID 13771494-[[4-(2-Methoxyphenyl)piperazin-1-yl]methyl]phenolYield 80%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

One mole of 4-hydroxyphenyl methanol (124 g) and 192 g (2 moles) of 1-(2-methoxyphenyl)piperazine were dissolved in 1.5 liters of toluene. One mole (87 g) of lithium bromide and 0.1 mole (5.6 g) of potassium hydroxide were added portionwise, under stirring, and the reaction medium was heated to reflux for 5 hours. The reaction mixture was then allowed to cool to room temperature, and extracted twice with 500 ml of a 1N sodium hydroxide. The basic aqueous liquor was washed with 300 ml of toluene and then acidified to pH 7 with acetic acid to provoke precipitation of the desired product. The precipitate thus obtained was filtered off and then recrystallized from isopropanol, giving 238.4 g (0.80 mole, 80% yield) of the title product, melting at 172° C.

Workup

  1. temperaturethe reaction medium was heated
  2. temperatureto reflux for 5 hours
  3. extractionextracted twice with 500 ml of a 1N sodium hydroxide
  4. washThe basic aqueous liquor was washed with 300 ml of toluene
  5. customprecipitation of the desired product
  6. customThe precipitate thus obtained
  7. filtrationwas filtered off
  8. customrecrystallized from isopropanol

Sources & evidence

ORD record
ord-2542dc2b32b146868b33d1740dd7134d
Source dataset
uspto-grants-1992_08
Patent number
US05142052

Linked notes

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