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(3S,4R)-4-(fluorophenyl)-3-hydroxymethyl-1-methyl piperidine and split method of antipodism thereof

A technology of methyl piperidine and p-fluorophenyl, which is applied in the field of high-performance liquid phase analysis and separation, can solve the problems of unsatisfactory resolution and unobtainable resolution methods, and achieve the effect of improving symmetry

Inactive Publication Date: 2008-04-02
BEIJING D VENTUREPHARM TECH DEV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The experimental results of repeating the method reported in the literature showed that (3S,4R)-4-(p-fluorophenyl)-3-hydroxymethyl-1-methylpiperidine and its enantiomers could not be resolved satisfactorily body, after repeated adjustments to the chromatographic conditions, the separation method that meets the resolution requirements of the Chinese Pharmacopoeia cannot be obtained

Method used

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  • (3S,4R)-4-(fluorophenyl)-3-hydroxymethyl-1-methyl piperidine and split method of antipodism thereof
  • (3S,4R)-4-(fluorophenyl)-3-hydroxymethyl-1-methyl piperidine and split method of antipodism thereof
  • (3S,4R)-4-(fluorophenyl)-3-hydroxymethyl-1-methyl piperidine and split method of antipodism thereof

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Experimental program
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Effect test

Embodiment 1

[0026] Instruments and conditions: High performance liquid chromatography: Japan Shimadzu: LC-10Avp, SPD-10Avp; Chromatographic column: OJ-H (250mm×4.6mm) chiral column; Mobile phase: n-hexane-isopropanol-triethyl Amine=97:3:0.5 (V:V:V); flow rate: 0.8 mL / min; detection wavelength: 266 nm; column temperature: room temperature; injection volume: 10 μL.

[0027] Experimental steps:

[0028] (1) Take 10mg of 4-(p-fluorophenyl)-3-hydroxymethyl-1-methylpiperidine racemate, put it in a 10mL volumetric flask, add methanol to dissolve and dilute to the scale, shake well, and use it as the test product solution.

[0029] (2) Take the reagent blank solution and the test solution respectively, carry out high-performance liquid chromatography analysis according to the above conditions, and record the chromatograms.

[0030] The results are shown in accompanying drawing 1, and what retention time is 10.667min is (3S, 4R)-4-(p-fluorophenyl)-3-hydroxymethyl-1-methylpiperidine, and what ret...

Embodiment 2

[0032] Instruments and conditions: High performance liquid chromatography: Japan Shimadzu: LC-10Avp, SPD-10Avp; Chromatographic column OD-RH (150mm×4.6mm) chiral column; Mobile phase: n-hexane-isopropanol-triethylamine =97:3:0.5 (V:V:V); flow rate: 0.8 mL / min; detection wavelength: 266 nm; column temperature: room temperature; injection volume: 10 μL.

[0033] Experimental steps:

[0034] (1) Take 10mg of the racemate of 4-(p-fluorophenyl)-3-hydroxymethyl-1-methylpiperidine, put it in a 10mL volumetric flask, add methanol to dissolve and dilute to the scale, shake well, and use it as the Test solution.

[0035] (2) Take the reagent blank solution and the test solution respectively, carry out high-performance liquid chromatography analysis according to the above conditions, and record the chromatograms.

[0036] Result is shown in accompanying drawing 2, and retention time is that (3S, 4R)-4-(p-fluorophenyl)-3-hydroxymethyl-1-methylpiperidine is 10.727min, and retention time ...

Embodiment 3

[0038] Instruments and conditions: High performance liquid chromatography: Japan Shimadzu: LC-10Avp, SPD-10Avp; Chromatographic column: OJ-H (250mm×4.6mm) chiral column; Mobile phase: n-hexane-methanol-triethylamine= 97:3:0.5 (V:V:V); flow rate: 0.8 mL / min; detection wavelength: 266 nm; column temperature: room temperature; injection volume: 10 μL.

[0039] Experimental steps:

[0040] (1) Take 10mg of the racemate of 4-(p-fluorophenyl)-3-hydroxymethyl-1-methylpiperidine, put it in a 10mL volumetric flask, add methanol to dissolve and dilute to the scale, shake well, and use it as the Test solution.

[0041] (2) Take the reagent blank solution and the test solution respectively, carry out high-performance liquid chromatography analysis according to the above conditions, and record the chromatograms.

[0042] The results are shown in Figure 3. What retention time is 19.067min is (3S, 4R)-4-(p-fluorophenyl)-3-hydroxymethyl-1-methylpiperidine, and what retention time is 23.667mi...

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Abstract

The present invention discloses a (3S, 4R)-4-(fluorophenyl)-3-hydroxymethyl-1-methyl piperidine and the high-efficiency liquid-phase method for disassembling enantiomers; the chiral column of cellulose category is used to change the n-hexane containing organic alkaline, an organic modifier, into the flow phase; the flow rate of the flow phase is 0.8mL / min. The present invention has good degree of separation.

Description

technical field [0001] The invention relates to a high-efficiency liquid phase analysis and separation method, in particular to a method using a cellulose-based chiral column, using n-hexane-organic modifier containing an organic base as the mobile phase, and resolving (3S, 4R)-4- A high performance liquid phase method for (p-fluorophenyl)-3-hydroxymethyl-1-methylpiperidine and its enantiomers. Background technique [0002] Paroxetine hydrochloride is an antidepressant drug that can treat various types of depression, obsessive-compulsive neurosis, social phobia, and social anxiety disorder. In the synthetic process of paroxetine, an intermediate whose chemical structure is as follows is involved, [0003] [0004] Its molecular formula is C 13 h 18 FNO, the chemical name is (3S,4R)-4-(p-fluorophenyl)-3-hydroxymethyl-1-methylpiperidine. The molecule of this intermediate contains 2 chiral carbon atoms, and a pair of enantiomers "(3S, 4R)-4-(p-fluorophenyl)-3-hydroxymeth...

Claims

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Application Information

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IPC IPC(8): C07D211/22C07B57/00
Inventor 胡杨
Owner BEIJING D VENTUREPHARM TECH DEV
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