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

HRID 1106369Notes

Reaction equation

HRID 1106369 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.Cl[CH2:9][CH2:10][OH:11].CC(C)=O>C(N(CC)CC)C>[OH:11][CH2:10][CH2:9][N:5]1[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]1

Participants

5

Reactant 3

HCID 342-ChloroethanolHCID 180AcetoneHCID 531671-Methylpiperazine

Product 1

HCID 2311841-(2-Hydroxyethyl)-4-methylpiperazineYield 75%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

N-methylpiperazine (10 g; 100 mmol) and 2-chloroethanol (8.05 g; 100 mmol) are stirred at 100° C. for 4 h. The highly viscous reaction medium is supplemented with 250 ml of acetone and the resulting suspension is neutralized with 15 ml of triethylamine. After filtration of the triethylamine hydrochloride, the solvent is evaporated under reduced pressure. The desired compound is obtained after purification by chromatography on an alumina column (Merck®; Aluminum Oxide 90; 63-200 μm, eluent: ethyl acetate) in the form of a colorless oil. Yield: 75%

Workup

  1. filtrationAfter filtration of the triethylamine hydrochloride
  2. customthe solvent is evaporated under reduced pressure

Sources & evidence

ORD record
ord-a212df5ae16e40908c8712cf535a877a
Source dataset
uspto-grants-2000_05
Patent number
US06056965

Reaction notes

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