4-Formylbenzoic acid → 4-(4-Methyl-1-piperazinylmethyl)benzoic acid

HRID 1170057Notes

Reaction equation

HRID 1170057 reaction equation
[CH:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1)=O.[CH3:12][N:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1.[H][H]>CO.[Pt]>[CH3:12][N:13]1[CH2:18][CH2:17][N:16]([CH2:1][C:3]2[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=2)[CH2:15][CH2:14]1

Participants

6

Reactant 3

HCID 120884-Formylbenzoic acidHCID 531671-MethylpiperazineHCID 178418361HCID 178418361, compound2×

Product 1

HCID 47697824-(4-Methyl-1-piperazinylmethyl)benzoic acidYield 70%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

A suspension of 4-formyl-benzoic acid (10.0 g, 67 mmol) in methanol (100 ml) is treated sequentially with 1-methylpiperazine (7.3 g, 73 mmol) and platinum (5%) on sulfided carbon (1 g). The resulting suspension is then heated at 80° C. and is subjected to a pressure of 5 bar of hydrogen for a period of 20 hrs until the hydrogen uptake is complete. The reaction mixture is cooled to room temperature and filtrated over a pad of Celite. Water (20 ml) is used to rinse the reactor and dissolve the fraction of 4-(4-methyl-piperazin-1-ylmethyl)-benzoic acid that crystallizes on the walls during the cooling of the reaction mixture. The resulting aqueous solution is filtrated over the pad of Celite employed previously. The combined filtrates are concentrated in vacuo and crystallized in EtOH/H2O 9:1 v/v to give 10.9 g (70%) of 4-(4-methyl-piperazin-1-ylmethyl)-benzoic acid as colorless crystals.

Workup

  1. temperatureThe reaction mixture is cooled to room temperature
  2. filtrationfiltrated over a pad of Celite
  3. washto rinse the reactor
  4. dissolutiondissolve the fraction of 4-(4-methyl-piperazin-1-ylmethyl)-benzoic acid
  5. customthat crystallizes on the walls during the
  6. temperaturecooling of the reaction mixture
  7. filtrationThe resulting aqueous solution is filtrated over the pad of Celite
  8. concentrationThe combined filtrates are concentrated in vacuo
  9. customcrystallized in EtOH/H2O 9:1 v/v

Sources & evidence

ORD record
ord-8e7fc62d0c32438d84aded6f83d48f34
Source dataset
uspto-grants-2010_11
Patent number
US07825247B2

Reaction notes

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