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Compound Name,Synthesization |
3.1 METHYLPHENIDATE (11968),"Methylphenidate (3.1.6) has been synthesized via condensation of phenylacetonitrile (3.1.1) with a 2-chloropyridin (3.1.2) at 110112C in toluene in the presence of NaNH2, which gave 2-phenyl-2-(pyridin-2-yl)acetonitrile (3.1.3). The last was hydrolyzed to corresponding amide (3.1.4), which on treatment with HCl in methanol on heating gave methyl 2-phenyl-2-(pyridin2-yl)acetate (3.1.5). Hydrogenation of the pyridine ring to a piperidine ring in the obtained product in acetic acid on the Pt or PtO2 catalyst gave the desired methylphenidate (3.1.6) [57] (Scheme 3.1)." |
3.2 PERHEXILINE (1216),"The synthesis of racemic perhexiline is based on nucleophilic addition of lithiated 2-picoline (3.1.7) to dicyclohexyl ketone (3.1.8) to give the corresponding tertiary alcohol (3.1.9), which undergoes HCL mediated dehydration forming alkene (3.1.10), the subsequent hydrogenation of which catalyzed by PtO2 gives desired perhexiline (3.1.11) [23,24]. An alternative approach was demonstrated, using as starting ketone, bezophenone (3.1.12), which on reaction with lithiated 2- picoline gives tertiary alcohol (3.1.13), which after dehydration using hydrochloric acid gives alkene (3.1.14), the hydrogenation of which catalyzed by PtO2 [25] or in presence Raney-Ni [26] or Rh-Al2O3 [27] gives desired perhexiline (3.1.11) (Scheme 3.2)." |
3.3 PIPRADROL (259),"Pipradrol (3.1.17) was synthesized from pyridyl Grignard reagent prepared from 2-pyridyl bromide (3.1.15) and bezophenone (3.1.12), which gave diphenylpydinemethanol (3.1.16) reduced catalytically to desired pipradrol (3.1.17) [31,32]. Enantiomers of pipradrol were synthesized from (R)- and (S)- pipecolic acid ethers (3.1.18) and the probable conformation of the base was deduced. All of the central stimulant activity resided in (R)-pipradrol, but both the (R) and (S) isomers possessed anticonvulsant properties [33] (Scheme 3.3)." |
3.4 MEFLOQUINE (5370),"The synthesis of mefloquine (3.1.27) began with the synthesis quinolin-4- ol (3.1.21) obtained by polyphosphoric acid condensation of the ethyl 4,4,4- trifluoroacetoacetate (3.1.19) with O-trifluoromethylaniline (3.1.20). A further conversion of prepared (3.1.21) by POBr3 into the 4-bromoquinoline (3.1.22) led to the transformation of the last 4-Li derivative (3.1.23) followed by CO2 carboxylation gave cinclioninic acid (3.1.24). Addition of 2-pyridyllithium (3.1.25) gave the pyridyl ketone (3.1.26). Hydrogenation with H2-PtO2 gave a good yield of desired mefloquine (3.1.27) [38,39] (Scheme 3.4)." |
3.5 MEPIVACAINE (4176),"Two basic methods for the synthesis of mepivacaine are proposed. The first comprises the transformation of ethyl 1-methylpipecolate (3.1.30) to 1-methylpiperidine-2-carboxylic acid amide with magnesium (2,6-dimethylphenyl) amide bromide (3.1.29) under reflux in ether. A magnesium derivative (3.1.29), in turn, was prepared via interaction of 2,6-xylidine (3.1.28) with ethylmagnesium bromide [4345]. In another method, picolinic acid was converted to its amide (3.1.32), hydrogenated over platinum on carbon catalyst, and alkylated at the piperidine ring nitrogen with formalin using palladium on carbon [43,45,46] (Scheme 3.5)." |
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