Potassium Hydroxide → 1-[2-(Diphenylmethoxy)ethyl]piperazine

HRID 652960Notes

Reaction equation

HRID 652960 reaction equation
[CH:1]([O:14][CH2:15][CH2:16][N:17]1[CH2:22][CH2:21][N:20](C(OCC)=O)[CH2:19][CH2:18]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+]>CO.O>[CH:1]([O:14][CH2:15][CH2:16][N:17]1[CH2:18][CH2:19][NH:20][CH2:21][CH2:22]1)([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 20196700N-(2-benzhydroxyethyl)-N'-ethoxycarbonylpiperazine

Product 1

HCID 6485251-[2-(Diphenylmethoxy)ethyl]piperazineYield 94.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

To a solution of 4.12 g (11.2 mmol) of the piperazine derivative in methanol (20 ml) and water (10 ml) was added 13.2 g (235 mmol) of of potassium hydroxide, and the mixture was refluxed for 19 hours. Water was added to the reaction mixture and the whole mixture was extracted with n-butanol. The organic layer was washed with water and concentrated by evaporation under reduced pressure. The residue was subjected to Sephadex column chromatography, eluted with methanol, to give 3.15 g (10.6 mmol) of N-(2-benzhydroxyethyl)piperazine.

Workup

  1. temperaturethe mixture was refluxed for 19 hours
  2. extractionthe whole mixture was extracted with n-butanol
  3. washThe organic layer was washed with water
  4. concentrationconcentrated by evaporation under reduced pressure
  5. washeluted with methanol

Sources & evidence

ORD record
ord-c03d6c2bf51e452f94af2f593bb8d641
Source dataset
uspto-grants-1987_06
Patent number
US04673684

Reaction notes

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