Sodium Hydroxide → 2-(4-Benzylpiperazin-2-yl)ethanol

HRID 1374738

Reaction equation

HRID 1374738 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([CH:9]([CH:13]1[CH2:18][N:17]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:16][CH2:15][NH:14]1)[C:10]([O-])=[O:11])C.[OH-].[Na+].S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1.O>[CH2:19]([N:17]1[CH2:16][CH2:15][NH:14][CH:13]([CH2:9][CH2:10][OH:11])[CH2:18]1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 24436Sodium SulfateHCID 21077878(RS)-ethyl-(4-benzylpiperazin-2-yl)acetateHCID 21226445Aluminium lithium hydride

Product 1

HCID 220219532-(4-Benzylpiperazin-2-yl)ethanolYield 91.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

A 1M solution of lithium aluminium hydride in tetrahydrofuran (32.8 ml) was added dropwise to a stirred solution of (RS)-ethyl-(4-benzylpiperazin-2-yl)acetate (D3) (4.3 g, 16.41 mmol) in anhydrous tetrahydrofuran (100 ml) under argon, maintaining the temperature below 10° C. The resultant was stirred for a further 0.25 h, warmed to room temperature and stirred for 2.5 h. Water (8.2 ml), 2N sodium hydroxide (10.2 ml), and water (8.2 ml) were added dropwise sequentially with ice cooling. After 0.2 h sodium sulfate was added, the mixture stirred for 0.2 h then filtered through a short pad of celite. The filtrate was evaporated in vacuo to give the title compound as a pale orange oil (3.3 g, 91%). Mass spectrum (AP+): Found 221 (MH+). C13H20N2O requires 220.

Workup

  1. temperaturemaintaining the temperature below 10° C
  2. stirringstirred for 2.5 h
  3. stirringthe mixture stirred for 0.2 h
  4. filtrationthen filtered through a short pad of celite
  5. customThe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-f4afc4719a024cb28b09b6415dcac3ff
Source dataset
uspto-grants-2007_01
Patent number
US07166608B2

Linked notes

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