ChemicalBook CAS DataBase List 3-PYRIDINAMINE, N-METHYL-4-(2-METHYLPHENYL)-6-(4-METHYL-1-PIPERAZINYL)-

3-PYRIDINAMINE, N-METHYL-4-(2-METHYLPHENYL)-6-(4-METHYL-1-PIPERAZINYL)- synthesis

13synthesis methods

Product Name:3-PYRIDINAMINE, N-METHYL-4-(2-METHYLPHENYL)-6-(4-METHYL-1-PIPERAZINYL)-
CAS Number:290297-25-5
Molecular formula:C18H24N4
Molecular Weight:296.41

342417-02-1 Synthesis

Methyl (6-(4-Methylpiperazin-1-yl)-4-(o-tolyl)pyridin-3-yl)carbaMate

342417-02-1
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3-PYRIDINAMINE, N-METHYL-4-(2-METHYLPHENYL)-6-(4-METHYL-1-PIPERAZINYL)-

290297-25-5
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Yield: 89%

Reaction Conditions:

with sodium bis(2-methoxyethoxy)aluminium dihydride in dichloromethane;toluene at 50; for 2 h;

Steps:

1.6 Synthesis of methyl-[6-(4-methyl-piperazin-1-yl)-4-o-tolyl-pyridin-3-yl]-amine
Step 6
A solution of 0.5 g (1.4 mMol) [6-(4-methyl-piperazin-1-yl)-4-o-tolyl-pyridin-3-yl]-carbamic acid methyl ester in 3.0 ml dichloromethane was added over 10 minutes to a solution of 1.98 ml (6.9 mMol) Red-Al (70% in toluene) and 2.5 ml toluene (exothermic, cool with a water bath to avoid temperature to go >50° C.).
The reaction mixture was stirred 2 hours at 50° C. in CH₂Cl₂, extracted with ethyl acetate and cooled to 0° C. 4 ml Aqueous NaOH 1N were carefully (exothermic) added over 15 minutes, followed by 20 ml ethyl acetate.
The phases were separated and the aqueous phase was extracted with ethyl acetate.
The combined organic extracts were washed with deionized water and brine, dried (Na₂SO₄) and concentrated under reduced pressure to yield 0.37 g (89%) methyl-[6-(4-methyl-piperazin-1-yl)-4-o-tolyl-pyridin-3-yl]-amine as an orange resin. MS (ISP): 297 (M+H⁺, 100).

References:

Helsinn Healthcare SA;Fadini, Luca;Manini, Peter;Pietra, Claudio;Giuliano, Claudio;Lovati, Emanuela;Cannella, Roberta;Venturini, Alessio;Stella, Valentino J. US8426450, 2013, B1 Location in patent:Page/Page column 26