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

HRID 2371208Notes

Reaction equation

HRID 2371208 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), CH2 Cl2 (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-f758aae1633d43f2bbda2366a51c8c32
Source dataset
uspto-grants-2014_04
Patent number
US08710224B2

Reaction notes

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