Methyl chloroacetate → (4-Methylpiperazin-1-yl)acetic acid

HRID 2400052Notes

Reaction equation

HRID 2400052 reaction equation
Cl[CH2:2][C:3]([O:5]C)=[O:4].[CH3:7][N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1.C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH3:7][N:8]1[CH2:13][CH2:12][N:11]([CH2:2][C:3]([OH:5])=[O:4])[CH2:10][CH2:9]1

Participants

5

Reactant 3

HCID 7295Methyl chloroacetateHCID 8471TriethylamineHCID 531671-Methylpiperazine

Product 1

HCID 2762732(4-Methylpiperazin-1-yl)acetic acidYield 70%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

165 g of methyl 2-chloroacetate are dropped into a solution of 152 g of N-methylpiperazine and 212 ml of triethylamine in 1.5 l of toluene, with stirring and under inert gas atmosphere; then the reaction mixture is heated to 70° C. for 4 hours. After that, the reaction mixture is cooled to room temperature, the resulting precipitate is filtered and washed on the filter with 100 ml of toluene. The resulting organic solution is extracted with water (5×200 ml) and the combined organic extracts are refluxed for about 20 hours, then water is distilled off under reduced pressure. The residue is crystallized from isopropanol, to obtain 168 g of 2-(N-methylpiperazino) acetic acid, m.p. 160°-161° C.

Workup

  1. temperatureAfter that, the reaction mixture is cooled to room temperature
  2. filtrationthe resulting precipitate is filtered
  3. washwashed on the
  4. filtrationfilter with 100 ml of toluene
  5. extractionThe resulting organic solution is extracted with water (5×200 ml)
  6. temperaturethe combined organic extracts are refluxed for about 20 hours
  7. distillationwater is distilled off under reduced pressure
  8. customThe residue is crystallized from isopropanol

Sources & evidence

ORD record
ord-40c02bf9e27b490d9581999e62787e3b
Source dataset
uspto-grants-1995_09
Patent number
US05453423

Reaction notes

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