2-Chloroethanol → 1-(2-Hydroxyethyl)-4-methylpiperazine

HRID 324768Notes

Reaction equation

HRID 324768 reaction equation
Cl[CH2:2][CH2:3][OH:4].[CH3:5][N:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:5][N:6]1[CH2:11][CH2:10][N:9]([CH2:2][CH2:3][OH:4])[CH2:8][CH2:7]1

Participants

5

Reactant 3

HCID 342-ChloroethanolHCID 11430Potassium CarbonateHCID 531671-Methylpiperazine

Product 1

HCID 2311841-(2-Hydroxyethyl)-4-methylpiperazineYield 77.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-Chloroethanol (36.0 g, 30 mL, 0.44 mol) was added to 1-methylpiperazine (27.0 g, 30 mL, 0.27 mol) and potassium carbonate (40 g, 0.29 mol) in acetonitrile (100 mL) with stirring. The reaction mixture was heated under reflux for 48 h, then filtered, and the solids were washed with acetonitrile. The combined filtrates were evaporated under reduced pressure and the resulting oil was distilled at 12 mm Hg to give the title compound (31 g, 0.21 mol) as a light tan oil. Electrospray MS m/z 145 [M+H]+.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 48 h
  3. filtrationfiltered
  4. washthe solids were washed with acetonitrile
  5. customThe combined filtrates were evaporated under reduced pressure
  6. distillationthe resulting oil was distilled at 12 mm Hg

Sources & evidence

ORD record
ord-766b638080674b3ea556afc7bd0c0880
Source dataset
uspto-grants-2001_04
Patent number
US06218538B1

Reaction notes

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