Sodium Hydroxide → 2-[4-(2-aminoethyl)piperazin-1-yl]ethanol

HRID 1064818Notes

Reaction equation

HRID 1064818 reaction equation
[C:1]([CH2:3][N:4]1[CH2:9][CH2:8][N:7]([CH2:10][CH2:11][OH:12])[CH2:6][CH2:5]1)#[N:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>C1COCC1.C(O)C>[NH2:2][CH2:1][CH2:3][N:4]1[CH2:9][CH2:8][N:7]([CH2:10][CH2:11][OH:12])[CH2:6][CH2:5]1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 22272590HCID 22272590, compound

Product 1

HCID 47424572-[4-(2-aminoethyl)piperazin-1-yl]ethanol

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 4-(cyanomethyl)piperazine-1-ethanol (1.69 g, 10 mmol) in THF (20 ml) was added to a solution of lithium aluminum hydride in THF (20 ml, 20 mmol) in an argon stream with ice cooling, the mixture was stirred at room temperature for 5 minutes and heated to reflux for 90 minutes. The reaction solution was allowed to cool, diluted with ethanol with ice cooling and stirred at room temperature for 15 minutes after adding an aqueous 1N sodium hydroxide solution thereto. This was filtered off through celite and the filtrate was concentrated in vacuo to provide 4-(aminoethyl)piperazine-1-ethanol.

Workup

  1. temperatureheated
  2. temperatureto reflux for 90 minutes
  3. temperatureto cool
  4. stirringstirred at room temperature for 15 minutes
  5. filtrationThis was filtered off through celite
  6. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-539c88751648429f939d960524738f57
Source dataset
uspto-grants-2005_11
Patent number
US06969711B2

Reaction notes

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