Hydrochloric Acid → 1,4-Dimethylpiperazine-2-carboxylic acid

HRID 603252Notes

Reaction equation

HRID 603252 reaction equation
C([O:3][C:4]([CH:6]1[CH2:11][N:10]([CH3:12])[CH2:9][CH2:8][N:7]1[CH3:13])=[O:5])C.[OH-].[Na+].Cl.CCOCC>CCO>[CH3:13][N:7]1[CH2:8][CH2:9][N:10]([CH3:12])[CH2:11][CH:6]1[C:4]([OH:5])=[O:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 2736419ethyl 1,4-dimethylpiperazine-2-carboxylate

Product 1

HCID 186850331,4-Dimethylpiperazine-2-carboxylic acidYield 48.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 1,4-dimethylpiperazin-2-yl carboxylic acid (1.86 g) was dissolved in EtOH (10 mL) and 5M aqueous NaOH (20 mL) added. The mixture was refluxed for 2 hours, allowed to cool, 10M HCl (9.1 mL) added to give pH4 and the mixture evaporated to dryness. The white solid was stirred with MeOH (25 mL), CH2Cl2 (10 mL) added and the filtrate evaporated to give, after trituration with Et2O, the title compound as a grey solid (761 mg, 48%).

Workup

  1. temperatureThe mixture was refluxed for 2 hours
  2. temperatureto cool
  3. customto give pH4
  4. customthe mixture evaporated to dryness
  5. additionadded
  6. customthe filtrate evaporated
  7. customto give

Sources & evidence

ORD record
ord-fe32eb0156d34e94a22331c6aa679761
Source dataset
uspto-grants-2011_03
Patent number
US07906645B2

Reaction notes

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