ChemicalBook CAS DataBase List 4-(4-Methylpiperazin-1-ylmethyl)benzoic acid

4-(4-Methylpiperazin-1-ylmethyl)benzoic acid synthesis

9synthesis methods

Product Name:4-(4-Methylpiperazin-1-ylmethyl)benzoic acid
CAS Number:106261-48-7
Molecular formula:C13H18N2O2
Molecular Weight:234.29

N-(4-methyl-3-((4-(pyridin-3-yl)thiazol-2-yl)amino)phenyl)-4-((4-methylpiperazin-1-yl)methyl)benzamide

728936-43-4

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

106261-48-7

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).

109-01-3 Synthesis

109-01-3
671 suppliers
$5.00/5 g

619-66-9 Synthesis

619-66-9
436 suppliers
$5.00/5g

106261-48-7
196 suppliers
$17.67/5gm:

Yield:106261-48-7 90%

Reaction Conditions:

with sodium tetrahydroborate;acetic acid in chloroform at 0 - 20; for 13 h;

Steps:

General procedure for the benzylation of 1-methylpiperazine (1). Synthesis of methyl 4-[(4-methylpiperazin-1-yl)methyl]benzoate (4a):
General procedure: AcOH (100%) (140 mL, 2.44 ml) was added over 1 h to a flask containing stirred NaBH₄ (20.0 g, 0.53 ml) and CHCl₃ (220 mL) at 0-5 °. The resulting mixture was stirred at 0-5 ° for 1.5 h and 1-methylpiperazine (1) (28.0 ml, 0.25 ml) and a solution of methyl 4-formylbenzoate (2a) (43.4 g, 0.26 ml) in CHCl₃ (60 mL) were added. The resulting mixture was stirred at 0-5 ° for 1 h and then for 12 h at rt. the mixture was treated with H₂O (150 mL) and Na₂CO₃ until pH 8.0-9.0. The aqueous phase was extracted with EtOAc (2 × 100 ml) then both organic layers were combined, washed with H₂O (1 × 100 ml), and dried over anhydrous Na₂SO₄. Filtration and evaporation of the solvents gave methyl 4-[(4-methylpiperazin-1-yl)methyl]benzoate (4a): yellowish oil; yield: 61.6 g, 99%.

References:

Koroleva, Elena V.;Kadutskii, Aleksey P.;Farina, Alexander V.;Ignatovich, Janna V.;Ermolinskaya, Anastasiya L.;Gusak, Klaudiya N.;Kalinichenko, Elena N. [Tetrahedron Letters,2012,vol. 53,# 38,p. 5056 - 5058] Location in patent:experimental part

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