Hydrochloric Acid → 4-(4-Methyl-1-piperazinylmethyl)benzoic acid

HRID 1455058Notes

Reaction equation

HRID 1455058 reaction equation
C[O:2][C:3](=[O:18])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:11]2[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]2)=[CH:6][CH:5]=1.O.Cl>[OH-].[K+].CO>[CH3:17][N:14]1[CH2:13][CH2:12][N:11]([CH2:10][C:7]2[CH:8]=[CH:9][C:4]([C:3]([OH:18])=[O:2])=[CH:5][CH:6]=2)[CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 782222Methyl 4-((4-methylpiperazin-1-yl)methyl)benzoate

Product 1

HCID 47697824-(4-Methyl-1-piperazinylmethyl)benzoic acid

Reagents, catalysts & solvents 1

HCID 23689386Potassium hydroxide methanolSolvent

Procedure

HCl-salt of 4-(4-methylpiperazin-1-ylmethyl)benzoic acid methyl ester (1.25 g) was dissolved in potassium hydroxide-methanol solution (0.93 g KOH in 15 ml methanol). Water (0.75 ml) was added and the mixture was refluxed for 1 hour. The reaction mixture was allowed to cool into room temperature and the pH was tuned to 6 with 2 M HCl. The solvent was evaporated and the residue was dried under vacuum. The residue contained 4-(4-methylpiperazin-1-ylmethyl)benzoic acid and inorganic salts. It was used further without purification and the yield of title compound was assumed to be 100%. 1H NMR (400 MHz, d6-DMSO) δ: 2.27 (s, 3H), 2.44 (bs, 2H), 3.18-3.95 (m, 8H), 7.41 (d, 2H, J 8.0 Hz), 7.89 (d, 2H, J 8.1 Hz).

Workup

  1. temperaturethe mixture was refluxed for 1 hour
  2. customThe solvent was evaporated
  3. customthe residue was dried under vacuum
  4. customIt was used further without purification

Sources & evidence

ORD record
ord-eca11c7f9a8e4857998a49910cba6c85
Source dataset
uspto-grants-2009_01
Patent number
US07482340B2

Reaction notes

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