overview[1]
1-(3-methylphenyl)piperazine dihydrochloride is a pharmaceutical intermediate, which is the hydrochloride form of 1-(3-methylphenyl)piperazine. it can be synthesized from 1-(3 -methylphenyl)piperazine is prepared from hydrogen chloride.
preparation method[1]
the general route to prepare 1-(3-methylphenyl)piperazine is as follows. reaction conditions: a.socl2, rt, 14-15h; b. 3-methylaniline, mw, 170℃-180℃, 30-45min
the specific operations are as follows:
synthesis of (β-chloroethyl)amine hydrochloride (x)
in a 100 ml flask, dissolve diethanolamine (10 g) in chloroform (40 ml), and slowly add a solution of sulfoxide dichloride (2.6 ml) in chloroform (20 ml) at room temperature. react for 7 hours. when the reaction is complete, spin it to dryness, add additional chloroform, spin it to dryness again, and evaporate the thionyl chloride to dryness. after drying, 14 g of white solid ix was obtained, with a yield of 85%, mp: 214.1-215.2°c (literature value >215-216°c).
synthesis of n-phenylpiperazine derivatives (xi)
add 1.58g (10mmol) ix and 1mol aniline derivative into 10ml n-butanol, react under microwave at 180°c for 30 minutes. after the reaction is completed, let it stand and cool to crystallize. filter, wash the filter cake with a small amount of methylene chloride, and dry it under vacuum to obtain white crystals (xi) with a yield of 45-54%.
apply[1]
cn103467456 reported that the free base of 1-(3-methylphenyl)piperazine dihydrochloride can be used to synthesize 3,5-disubstituted indolinone derivatives such as: 3-((1h-pyrrole- 2-yl)methenyl)-5-(4-(m-methylphenyl)piperazine-1-carbonyl)indol-2-one (compound 30), this 3,5-disubstituted indolinone derivatives can be used to prepare mapk inhibitors and akt inhibitors, thereby preparing anti-lung cancer drugs. the structure is as follows:
main reference materials
[1] (cn103467456) 3,5-disubstituted indolinone derivatives and preparation methods and applications
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