4-(4-Methylpiperazin-1-ylmethyl)benzoic acid Chemical Properties

Melting point:

310-312 °C

Boiling point:

377.2±32.0 °C(Predicted)

Density 

1.174±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

4.31±0.10(Predicted)

Appearance

White to off-white Solid

Water Solubility 

Slightly soluble in water.

4-(4-Methylpiperazin-1-ylmethyl)benzoic acid Usage And Synthesis

Uses

4-(4-Methyl-1-piperazinylmethyl)benzoic acid is used as Imatinib intermediate, as pharmaceutical intermediate.

Synthesis

GENERAL STEPS: Methyl 4-(4-methylpiperazin-1-ylmethyl)benzoate hydrochloride (1.25 g) was dissolved in potassium hydroxide-methanol solution (0.93 g KOH dissolved in 15 ml methanol). Water (0.75 ml) was added and the mixture was heated to reflux for 1 hour. After completion of the reaction, the mixture was cooled to room temperature and the pH was adjusted to 6 with 2 M hydrochloric acid solution. the solvent was removed by evaporation and the residue was dried under vacuum. The resulting residue contained 4-(4-methylpiperazin-1-ylmethyl)benzoic acid and the inorganic salt, which could be used in the subsequent reaction without further purification, assuming 100% yield of the title compound.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=8Hz), 7.89 (d, 2H, J=8.1Hz).

References

[1] Patent: WO2004/63191, 2004, A1. Location in patent: Page 74

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