Methyl chloroacetate → Methyl (4-methylpiperazin-1-yl)acetate

HRID 34270Notes

Reaction equation

HRID 34270 reaction equation
Cl[CH2:2][C:3]([O:5][CH3:6])=[O:4].[CH3:7][N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1>C(OCC)(=O)C>[CH3:7][N:8]1[CH2:13][CH2:12][N:11]([CH2:2][C:3]([O:5][CH3:6])=[O:4])[CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 7295Methyl chloroacetateHCID 531671-Methylpiperazine

Product 1

HCID 6422228Methyl (4-methylpiperazin-1-yl)acetateYield 95%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Methyl chloroacetate (8.8 ml., 0.10 mole) was added to a solution of N-methylpiperazine (24.4. ml., 0.22 mole) in ethyl acetate (140 ml.) and the mixture was stirred for 17 hours. The reaction mixture was filtered and the solvent was removed under vacuum. The resulting oil was dissolved in methylene chloride-methanol (9:1) and purified by flash chromatography (silica) to give 2-(4-methyl-1-piperazinyl)acetic acid, methyl ester as an oil (16.3 g, 95%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe solvent was removed under vacuum
  3. dissolutionThe resulting oil was dissolved in methylene chloride-methanol (9:1)
  4. custompurified by flash chromatography (silica)

Sources & evidence

ORD record
ord-91b37a5954d74ff795689c1a0561d58a
Source dataset
uspto-grants-1988_08
Patent number
US04761415

Reaction notes

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