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A process for producing acetylnorbornene, an intermediate in the synthesis of biperiden

A kind of norbornene and acetyl technology, which is used in the field of preparing the intermediate acetyl norbornene used in the synthesis of biperiden, and can solve the problems of high toxicity, difficulty in handling, and inability to fully satisfy industrial production.

Inactive Publication Date: 2009-12-09
SAIRAM ORGANICS PVT
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, the starting material methyl vinyl ketone used in the method of the prior art has the disadvantage that it is not very stable and will polymerize on standing
Moreover, methyl vinyl ketone is expensive and difficult to handle due to its highly toxic characteristics
Due to the highly exothermic reaction of cyclopentadiene and methyl vinyl ketone, the degree of scale-up of the reaction is limited, so this traditional method cannot fully meet the needs of industrial production

Method used

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  • A process for producing acetylnorbornene, an intermediate in the synthesis of biperiden
  • A process for producing acetylnorbornene, an intermediate in the synthesis of biperiden
  • A process for producing acetylnorbornene, an intermediate in the synthesis of biperiden

Examples

Experimental program
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Effect test

Embodiment 1

[0017] Preparation of 5-Cyanonorbornene

[0018] To a solution of acrylonitrile (249.4 g, 4.7 moles) in methanol (260 mL) was slowly added cyclopentadiene monomer (311.0 g, 4.7 moles) over 45 minutes at 40°C. The reaction temperature was maintained at 40 to 50°C for 1 hour. The solvent was removed under vacuum to give a residue (487.3 g), which was distilled under high vacuum to give 5-cyanonorbornene (453.3 g, 80.8% yield).

Embodiment 2

[0020] Preparation of 5-acetyl norbornene

[0021] 1,4-Dioxane was slowly added to a solution of methylmagnesium chloride (263.6 mL, 3.0 M in THF, 0.53 mol) at room temperature over 1 hour. 5-Cyanonorbornene (30 g, 0.25 mol) was then added slowly at room temperature over 1 hour and the reaction mixture was refluxed for 90 minutes. After the reaction was complete, the reaction mixture was cooled and poured into ice-cold water (200 mL). Acetylnorbornene (25.5 g, 75% yield) prepared by vacuum distillation was routinely tested. The ratio of exo to endo isomer was 1.8 [gas chromatography analysis (area %): exo / endo=41.80 / 23.16=1.8].

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Abstract

The present invention relates to a novel process for the production of acetylnorbornene, efficiently and industrially useful manner. The process is applicable for the large scale production of acetylnorbornene and consists of preparation of 5-cyanonorbornene and its reaction with appropriate Grignard reagents. The product contains higher proportion of the exo form than the endo form, which is important for the synthesis of biperiden.

Description

technical field [0001] The present invention relates to a novel method for preparing acetylnorbornene, which is an intermediate in the synthesis of biperiden. In particular, the present invention relates to a process for the preparation of acetylnorbornene, which is necessary for the synthesis of biperiden and contains a higher proportion of the exo form than the endo form. The method is applicable for the large-scale production of acetylnorbornene and consists of the preparation of 5-cyanonorbornene and its reaction with an appropriate Grignard reagent. Background technique [0002] The exo-form of 5-acetylnorbornene is a key intermediate in the synthesis of the anticholinergic (anticholinergic) anti-Parkinson's drug biperiden (I). [0003] [0004] The traditional method is to synthesize 5-acetylnorbornene through the Diels-Alder reaction of cyclopentadiene and methyl vinyl ketone (Scheme 1). [0005] [0006] Schema 1 [0007] The products produced by this tradit...

Claims

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Application Information

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IPC IPC(8): C07C45/00
CPCC07C253/30C07C49/323C07C45/004C07C2102/42C07C2602/42
Inventor 芬卡塔·宿巴拉居·高突木卡拉拉姆巴得拉·萨玛·玛米拉帕里芝然基夫·特里
Owner SAIRAM ORGANICS PVT
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