1-(2-Hydroxyethyl)piperazine → HCID 22272590, compound

HRID 1064817Notes

Reaction equation

HRID 1064817 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:17][C:18]#[N:19]>C(#N)C>[C:18]([CH2:17][N:7]1[CH2:8][CH2:9][N:4]([CH2:3][CH2:2][OH:1])[CH2:5][CH2:6]1)#[N:19]

Participants

5

Reactant 3

HCID 76771-(2-Hydroxyethyl)piperazineHCID 7856ChloroacetonitrileHCID 11430Potassium Carbonate

Product 1

HCID 22272590HCID 22272590, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 1-(2-hydroxyethyl)piperazine (2.60 g, 20 mmol) in acetonitrile (35 ml) was added potassium carbonate (3.04 g, 22 mmol) and chloroacetonitrile (1.51 g, 20 mmol) was dropped thereinto with ice cooling. The mixture was stirred at room temperature for 30 minutes and then stirred at 45° C. for 30 minutes. This reaction mixture was filtered off, the filtrate was concentrated in vacuo and the residue was purified by a silica gel column chromatography (100 g of silica gel; developing solvent, chloroform:ammonia-saturated methanol=20:1→10:1) to provide 3.20 g (yield 95%) of 4-(cyanomethyl)piperazine-1-ethanol.

Workup

  1. additionwas dropped
  2. stirringstirred at 45° C. for 30 minutes
  3. filtrationThis reaction mixture was filtered off
  4. concentrationthe filtrate was concentrated in vacuo
  5. customthe residue was purified by a silica gel column chromatography (100 g of silica gel; developing solvent, chloroform:ammonia-saturated methanol=20:1→10:1)

Sources & evidence

ORD record
ord-936ecfab76e64f38a98714768ecd7c58
Source dataset
uspto-grants-2005_11
Patent number
US06969711B2

Reaction notes

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