Hydrochloric Acid → 4-((3-Oxopiperazin-1-yl)methyl)benzoic acid

HRID 225503

Reaction equation

HRID 225503 reaction equation
BrC[C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([OH:8])=[O:7].[NH:12]1[CH2:17][CH2:16][NH:15][CH2:14][C:13]1=[O:18].[C:19](=O)([O-])[O-].[K+].[K+].Cl>CO>[O:18]=[C:13]1[NH:12][CH2:17][CH2:16][N:15]([CH2:19][C:11]2[CH:3]=[CH:4][C:5]([C:6]([OH:8])=[O:7])=[CH:9][CH:10]=2)[CH2:14]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 231360Piperazin-2-oneHCID 2456503-(Bromomethyl)benzoic acid

Product 1

HCID 167770994-((3-Oxopiperazin-1-yl)methyl)benzoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 3-bromomethylbenzoic acid (4.30 g, 20 mmol), piperazin-2-one (2.0 g, 20 mmol) and powdered potassium carbonate (2.76 g, 20 mmol) in methanol (50 mL) is stirred for 17 hours at room temperature. The resulting mixture is filtered and the solvent is evaporated off under reduced pressure to give a residue which is treated with hydrochloric acid (80 mL of 0.25 M) and stirred for 5 min. The precipitated product is filtered, washed with water, dried and recrystallised from methanol to give the title compound as a cream crystalline solid.

Workup

  1. filtrationThe resulting mixture is filtered
  2. customthe solvent is evaporated off under reduced pressure
  3. customto give a residue which
  4. stirringstirred for 5 min
  5. filtrationThe precipitated product is filtered
  6. washwashed with water
  7. customdried
  8. customrecrystallised from methanol

Sources & evidence

ORD record
ord-d2829c2fd933447e93829e3a197b0e72
Source dataset
uspto-grants-2009_07
Patent number
US07557105B2

Linked notes

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