1-(2-Hydroxyethyl)piperazine → HCID 21254464, compound

HRID 2226674Notes

Reaction equation

HRID 2226674 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1.[ClH:10].[CH2:11]([Cl:13])[CH3:12].[OH-].[Na+]>O>[ClH:13].[ClH:10].[ClH:13].[CH2:3]([N:4]([CH2:11][CH3:12])[CH2:5][CH2:6][N:7]1[CH2:8][CH2:9][N:4]([CH2:3][CH2:2][OH:1])[CH2:5][CH2:6]1)[CH3:2]

Participants

5

Reactant 3

HCID 76771-(2-Hydroxyethyl)piperazineHCID 14798Sodium HydroxideHCID 21954268HCID 21954268, compound

Product 1

HCID 21254464HCID 21254464, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of 76.0 g (0.58 mol) of 1-(2-hydroxyethyl)piperazine in 200 ml of water was added dropwise 201.0 g (0.58 mol) of a 50% aqueous solution of 2-diethylamino)ethyl chloride hydrochloride. The pH was maintained at 10 by addition of 25% NaOH while the solution was stirred for 18 hours. Water was removed to give a thick oil which was extracted with ethanol. The ethanolic solution was filtered, then the ethanol was removed. The resulting liquid was distilled to give 67.7 g (51%) (b.p. 110°-112° C./0.1 Torr) of the alcohol as a light brown liquid. The trihydrochloride salt was prepared by acidifying the free base to a pH of 1 and removing the water.

Workup

  1. customWater was removed
  2. customto give a thick oil which
  3. extractionwas extracted with ethanol
  4. filtrationThe ethanolic solution was filtered
  5. customthe ethanol was removed
  6. distillationThe resulting liquid was distilled

Sources & evidence

ORD record
ord-059e21d492d54fa6a35581eb7353b2e2
Source dataset
uspto-grants-1994_09
Patent number
US05349089

Reaction notes

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