WO2002090339A1 - Procede de preparation de 1-methyl-3-phenyl-piperazine - Google Patents
Procede de preparation de 1-methyl-3-phenyl-piperazine Download PDFInfo
- Publication number
- WO2002090339A1 WO2002090339A1 PCT/IN2002/000117 IN0200117W WO02090339A1 WO 2002090339 A1 WO2002090339 A1 WO 2002090339A1 IN 0200117 W IN0200117 W IN 0200117W WO 02090339 A1 WO02090339 A1 WO 02090339A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- stirring
- phenyl
- piperazine
- temperature
- product
- Prior art date
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/04—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
Definitions
- the present invention pertains to the pharmaceutical industry in general novel process for preparing 1- Methyl-3-phenyl piperazine without impurities.
- Patent 4772705 wherein its preparation was reported as starting from cthylenc diaminc and ethyl a- bromophenyl acetate in absolute ethanol to give 3-phenyl-2-pipcrazinone which on reduction with lithium aluminium hydride in anhydrous ether gave 2-phenyl piperazine which was methylated with methyl iodide in presence of acetone and triethvlamine and isolated as its hydrochloride in 54% yield. Methylation of 2-phenyl piperazine by this method gives undesired side products, which are difficult to be eschewed or removed. The above process is time consuming and expensive. Besides the obtained process is full of impurities.
- a process for preparing l-Methyl-3-phenyl-p ⁇ peraz ⁇ ne which comprises: (i) mixing l-Benzyl-2-phenyl piperazine with formic acid solution while stirring and then with formaldehyde solution and heating the mixture to a temperature of 70°C to 80°C for 50 to 70 minutes;
- Step (ii) reheating the obtained solution of Step (i) to a temperature of
- Step (iv) washing the product of Step (iii) with water and drying to obtain l-Bcnzyl-4-mcthyl-2-phenyl piperazine;
- Step (v) adding the product of Step (iv) with acetic acid taken in hydrogenator in the presence of palladium-carbon catalyst under nitrogen atmosphere while continuously stirring the mixture for about
- Methyl-3-phenyl piperazine is highly imperative for preparation of the anti-depressant drug, which is known as Mirtazapine.
- l-Methyl-3-phenyl piperazine is free from impurities.
- reaction mass gets added to sodium hydroxide solution (5% w/v; 2800 ml) by maintaining the temperature below 25°C.
- sodium hydroxide solution 5% w/v; 2800 ml
- the contents get stirred for one hour and thereby filtered.
- the product is then washed with water (1000 ml), sucked well and dried to a constant weight at 50 to 55 (J C to yield 361g of the product (m.p
- Acetic acid is distilled completely under vacuum, demineralised water (300 ml) is added to the residue and to this under stirring sodium hydroxide solution (50% w/v, 400ml) gets added maintaining the temperature below 25°C.
- the contents are then extracted twice with hexane (1000 ml and 500 ml).
- the hexane layer is concentrated to 200 ml, cooled 0 to 5°C, stirred for 50 to 70 minutes at 0 to 5 ⁇ C and filtered.
- the product is then washed with chilled hexane (50 ml), sucked well dried to a constant weight in an air oven to yield 106g of the product, (m.p. 53 to 55°C, 80.1% yield).
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
IN364CH2001 | 2001-05-08 | ||
IN364/MAS/2001 | 2001-05-08 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2002090339A1 true WO2002090339A1 (fr) | 2002-11-14 |
Family
ID=11096997
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/IN2002/000117 WO2002090339A1 (fr) | 2001-05-08 | 2002-05-06 | Procede de preparation de 1-methyl-3-phenyl-piperazine |
Country Status (1)
Country | Link |
---|---|
WO (1) | WO2002090339A1 (fr) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2004106309A1 (fr) * | 2003-06-02 | 2004-12-09 | Aurobindo Pharma Ltd | Procede de preparation de 1-methyl-3-phenylpiperazine |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4772705A (en) * | 1985-07-25 | 1988-09-20 | Pennwalt Corporation | Processes for the preparation of trans 1,3,4,6,7,11b-hexahydro-7-aryl-2H-pyrazinol[2,1-a]isoquinolines |
-
2002
- 2002-05-06 WO PCT/IN2002/000117 patent/WO2002090339A1/fr not_active Application Discontinuation
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4772705A (en) * | 1985-07-25 | 1988-09-20 | Pennwalt Corporation | Processes for the preparation of trans 1,3,4,6,7,11b-hexahydro-7-aryl-2H-pyrazinol[2,1-a]isoquinolines |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2004106309A1 (fr) * | 2003-06-02 | 2004-12-09 | Aurobindo Pharma Ltd | Procede de preparation de 1-methyl-3-phenylpiperazine |
US7041826B2 (en) * | 2003-06-02 | 2006-05-09 | Aurobindo Pharma Ltd. | Process for preparing 1-methyl-3-phenylpiperazine using a novel intermediate |
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