Synthesis and HPLC Enantioseparation of Derivatives of the 3-hydroxyphenylethanone

Cizmáriková, R; Némethy, Andrej; Valentová, Jindra; Hroboňová, Katarína; Bruchatá, Katarína

doi:10.2478/v10219-012-0023-7

Cited by 2 publications

(1 citation statement)

References 20 publications

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“…The purity of the final products was checked by thin-layer chromatography using ethyl acetate/diethylamine as the mobile phase ( Table 1). The structures of prepared compounds were confirmed by IR, UV and 1 H NMR, 13 C NMR spectra (Tables 2-4). The stretching vibration of the characteristic group in the IR spectra were ν(OH) 3166-3400 cm -1 , ν(NH) (base) 3073-3274 cm -1 , ν(C=C) 1578-1604 cm -1 , ν(C=O) 1668-1682 cm -1 , ν(CAl OCAr) 1251-1276 cm -1 ( Table 2).…”

Section: Resultsmentioning

confidence: 99%

Synthesis of new compounds of the aryloxyaminopropanol type and their HPLC enantioseparation

Cizmáriková¹,

Némethy²,

Valentová³

et al. 2013

Acta Facultatis Pharmaceuticae Universitatis Comenianae

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This article describes a preparation of some new compounds of the aryloxyaminopropanol type derived from 4-hydroxyphenylpropan- 1-one with phenylamino, cyclohexylamino and isobutylamino group in the hydrophilic part and methoxymethyl or ethoxymethyl substituent in the lipophilic part of the molecule. The purity of the prepared compounds was checked by thinlayer chromatography and the structure was confirmed on the basis of interpretation of the IR, UV, 1H NMR and 13C NMR spectra. An enantioseparation of the prepared compounds was performed by using high-performance liquid chromatography on an amylase tris(3,5-dimethylphenylcarbamate) (Chiralpak AD) and native teicoplanin (Chirobiotic T). The chromatographic results such as retention, separation and resolution factors have shown that Chiralpak AD is more suitable for enantioseparation of some of the prepared compounds.

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Section: Resultsmentioning

confidence: 99%

Synthesis of new compounds of the aryloxyaminopropanol type and their HPLC enantioseparation

Cizmáriková¹,

Némethy²,

Valentová³

et al. 2013

Acta Facultatis Pharmaceuticae Universitatis Comenianae

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Synthesis and HPLC enantioseparation of novel derivatives of 3-alkoxy-4-hydroxyphenylalkanones of a potential α/β-blocker type

Cizmáriková¹,

Habala²,

Valentová³

et al. 2021

Čes. slov. farm.

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The present paper reports the synthesis of a series of seven compounds with a hetero aminopropanol chain. The compounds were prepared by the conversion of 3-alkoxy-4-hydroxyphenyl alkanones with 2-chloromethyl oxirane and subsequent reaction of the products with heterocyclic amines (pyrrolidine, azepane, 4-methylpiperazine and 2-methoxyphenyl piperazine). The target compounds were synthesized in the form of racemates. The purity of the products was confirmed by thin layer chromatography and their IR, UV-VIS and 1H-NMR spectra were recorded. Enantioseparation of the racemic products was accomplished by HPLC on a Chiralpak AD chiral chromatographic column with tris(3,5-dimethylphenyl)carbamate as the chiral selector. The efficiency of enantioseparation was determined in relation to the composition of the mobile phase (hexane : ethanol : methanol : ethylethanamine) and to the structure of the prepared compounds. Baseline separation was achieved with all compounds using mobile phases A (78 : 11 : 11 : 0,1 v/v/v/v) and B (80 : 10 : 10 : 0,1 v/v/v/v), with selectivity factor ranging from 1.07 to 1.42 and resolution from 0.76 to 5.47. The mobile phase containing a higher amount of hexane did not allow for successful enantioseparation of the piperazine derivatives.

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Synthesis and HPLC Enantioseparation of Derivatives of the 3-hydroxyphenylethanone

Cited by 2 publications

References 20 publications

Synthesis of new compounds of the aryloxyaminopropanol type and their HPLC enantioseparation

Synthesis of new compounds of the aryloxyaminopropanol type and their HPLC enantioseparation

Synthesis and HPLC enantioseparation of novel derivatives of 3-alkoxy-4-hydroxyphenylalkanones of a potential α/β-blocker type

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