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Amine derivatives of the beta-farnesene

A technology of farnesene and farnesamide, which is applied in the field of amine derivatives and can solve problems such as ineffective reactions

Inactive Publication Date: 2019-07-19
CLARIANT INT LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The use of β-farnesene in hydroaminations is particularly challenging because the reaction of the very nonpolar farnesene with polar amines can result in a heterogeneous reaction solution in which the reaction cannot be efficiently

Method used

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  • Amine derivatives of the beta-farnesene
  • Amine derivatives of the beta-farnesene
  • Amine derivatives of the beta-farnesene

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0069] Weigh 16.6 mg of Pd(hfacac) in a 25 mL steel autoclave 2 and 109.3 mg of DPPB and dissolved in 5 mL of DMF. Then 817.4 mg of β-farnesene and 296.9 mg of diethylamine were added. The reactor was closed and loaded with argon pressure of 5 bar.

[0070] The reactor was heated at 100 °C for 5 h and stirred at 500 rpm by means of a magnetic stirrer. To terminate the reaction, the reactor was cooled to room temperature and then argon was carefully vented.

[0071] The obtained reaction solution was freed of solvent under vacuum and the product was purified by column chromatography. 863.2 mg (78%) of the hydroaminated product were obtained.

Embodiment 2

[0073] Weigh 10.6 mg of Pd(tfa) in a 25 mL steel autoclave 2 and 137.8 mg of DPEPhos and dissolved in 5 mL of methanol. Then 817.7 mg of β-farnesene and 297.1 mg of diethylamine were added. The reactor was closed and loaded with argon pressure of 5 bar.

[0074] The reactor was heated at 100 °C for 5 h and stirred at 500 rpm by means of a magnetic stirrer. To terminate the reaction, the reactor was cooled to room temperature and then argon was carefully vented.

[0075] The obtained reaction solution was freed of solvent under vacuum and the product was purified by column chromatography. 960.4 mg (89%) of the hydroaminated product were obtained.

Embodiment 3

[0077] Weigh 10.5 mg of Pd(tfa) in a 25 mL steel autoclave 2 and 137.7 mg of DPEPhos and dissolved in 5 mL of anisole. Then 816.8 mg of β-farnesene and 516.6 mg of dibutylamine were added. The reactor was closed and loaded with argon pressure of 5 bar.

[0078] The reactor was heated at 100 °C for 5 h and stirred at 500 rpm by means of a magnetic stirrer. To terminate the reaction, the reactor was cooled to room temperature and then argon was carefully vented.

[0079] The obtained reaction solution was freed of solvent under vacuum and the product was purified by column chromatography. 960.8 mg (72%) of the hydroaminated product were obtained.

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Abstract

The invention relates to a method for producing farnesyl amines by reacting beta-farnesene with one or more amines in the presence of a transition metal catalyst of the10th subgroup, at a temperaturein the region of between 60-150 DEG C.

Description

technical field [0001] The present invention relates to the preparation of amine derivatives of β-farnesene by metal-catalyzed addition of amines to the 1,3-diene unit of farnesene. These products are especially important intermediates in the synthesis of perfumes, and the downstream products of farnesamide also have surface-active properties. Background technique [0002] Industrially, terpene amines are prepared by the reaction of terpenes, such as β-myrcene, with amines in the presence of elemental sodium. Within the framework of the Takasago process, (-)-menthol is thus produced in a multistep process starting from β-myrcene. [0003] Analogously to this, the hydroamination of β-farnesene with organolithium compounds is also described in various publications (EP-A-2 894143). The products of the examples are intermediates in perfume synthesis. [0004] One of the disadvantages of base-catalyzed hydroamination is the incompatibility with protic solvents such as alcohols...

Claims

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Application Information

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IPC IPC(8): C07C209/60C07C211/21C07C211/27C07C211/48C07C213/02C07C215/10
CPCC07C209/60C07C213/02C07C211/21C07C215/10C07C211/27C07C211/48B01J27/10B01J31/2239B01J31/2404B01J2231/44B01J2531/824B01J2531/847C07C217/46Y02P20/584
Inventor D·莱因韦伯尔R·罗曼斯基A·沃霍尔特A·贝尔T·A·法斯巴赫
Owner CLARIANT INT LTD
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