Sodium Hydroxide → 2-(1-Benzylpiperazin-2-yl)ethanol

HRID 2117255Notes

Reaction equation

HRID 2117255 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:9][C:10](=O)[CH2:11][CH:12]1[C:17](=O)[NH:16][CH2:15][CH2:14][N:13]1[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)C.[OH-].[Na+]>C1COCC1>[CH2:19]([N:13]1[CH2:14][CH2:15][NH:16][CH2:17][CH:12]1[CH2:11][CH2:10][OH:9])[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 12317429Ethyl 2-(1-benzyl-3-oxopiperazin-2-yl)acetateHCID 21226445Aluminium lithium hydride3×

Product 1

HCID 508533142-(1-Benzylpiperazin-2-yl)ethanolYield 90.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminum hydride (4.6 grams, 120 mmol) was slowly added to a solution of (1-benzyl-3-oxo-piperazin-2-yl)-acetic acid ethyl ester (11 g, 40 mmol) in THF (150 mL) at 0° C. The mixture was allowed to stir for 18 h while warming to RT. The mixture was placed in and ice/water bath and additional lithium aluminum hydride (3.0 g, 80 mmol) was added. The mixture was allowed to stir for 20 h while warming to RT. 1 N NaOH was added until all of the LAH was consumed resulting in a white solid. The mixture was filtered through a pad of celite, washing with additional THF (50 mL). The filtrate was concentrated in vacuo to give 8 g (90%) of the title compound as an oil: APCI MS m/z 221.2 (M+1).

Workup

  1. stirringto stir for 20 h
  2. temperaturewhile warming to RT
  3. customwas consumed
  4. customresulting in a white solid
  5. filtrationThe mixture was filtered through a pad of celite
  6. washwashing with additional THF (50 mL)
  7. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-55830877faa44d64878c0e92a7aa59de
Source dataset
uspto-grants-2008_10
Patent number
US07442694B2

Reaction notes

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