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WO2011069994A1 - Procédé de production de 2,2-difluoréthylamine et de ses sels à partir de difluoracétonitrile - Google Patents

Procédé de production de 2,2-difluoréthylamine et de ses sels à partir de difluoracétonitrile Download PDF

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Publication number
WO2011069994A1
WO2011069994A1 PCT/EP2010/069036 EP2010069036W WO2011069994A1 WO 2011069994 A1 WO2011069994 A1 WO 2011069994A1 EP 2010069036 W EP2010069036 W EP 2010069036W WO 2011069994 A1 WO2011069994 A1 WO 2011069994A1
Authority
WO
WIPO (PCT)
Prior art keywords
acid
formula
butyl
difluoroethylamine
iii
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/EP2010/069036
Other languages
German (de)
English (en)
Inventor
Norbert Lui
Stefan Antons
Wahed Ahmed Moradi
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer CropScience AG
Original Assignee
Bayer CropScience AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority to EP10798990.7A priority Critical patent/EP2509937B1/fr
Priority to ES10798990.7T priority patent/ES2524304T3/es
Priority to JP2012542506A priority patent/JP5734997B2/ja
Priority to CN201080055886.XA priority patent/CN102741218B/zh
Priority to IN5122DEN2012 priority patent/IN2012DN05122A/en
Priority to DK10798990.7T priority patent/DK2509937T3/en
Priority to KR1020127017811A priority patent/KR101788083B1/ko
Priority to BR112012014046-9A priority patent/BR112012014046A2/pt
Priority to MX2012006590A priority patent/MX2012006590A/es
Application filed by Bayer CropScience AG filed Critical Bayer CropScience AG
Publication of WO2011069994A1 publication Critical patent/WO2011069994A1/fr
Priority to IL219711A priority patent/IL219711A/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/12—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups
    • C07C233/13—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/62—Preparation of compounds containing amino groups bound to a carbon skeleton by cleaving carbon-to-nitrogen, sulfur-to-nitrogen, or phosphorus-to-nitrogen bonds, e.g. hydrolysis of amides, N-dealkylation of amines or quaternary ammonium compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/06—Preparation of carboxylic acid amides from nitriles by transformation of cyano groups into carboxamide groups

Definitions

  • the present invention relates to a process for the preparation of 2,2-difluoroethylamine of the formula (I) and its salts, such as, for example, sulfates, hydrochlorides or acetates, starting from difluoroacetonitrile.
  • 2,2-Difluoroethylamine and its salts are important intermediates for the preparation of active ingredients, in particular agrochemical active ingredients.
  • Various production methods for 2,2-difluoroethylamine are known.
  • Donetti et al. J. Med. Chem. 1989, 32, 957-961
  • J. Med. Chem. 1989, 32, 957-961 describe, for example, the synthesis of 2,2-difluoroethylamine hydrochloride starting from 2,2-difluoroacetamide, in which the corresponding amide is treated with a diborane solution in tetrahydrofuran (THF). is reduced.
  • Kluger et al. JACS 1982, 104, 10, 2891-2897 describe the reduction of 2,2-difluoroacetamide with sodium borohydride and boron trifluoride etherate to 2,2-difluoroethylamine.
  • An inexpensive production process consists in the hydrogenation of difluoroacetonitrile, which is readily available as starting material. It can be prepared, for example, from difluoroacetamide (Swarts et al., Bulletin Societes Chimiques Beiges 1922, 31, 364-5), Grunewald et al., J. Med. Chem. 2006, 49 (10), 2939-2952).
  • the catalytic hydrogenation of trifluoroacetonitrile using PtZ 2 is described by Gilman et al. (JACS 1943, 65 (8), 1458-1460) to give trifluoroethylamine hydrochloride.
  • 2,2-difluoroethylamine of the formula (I) can be obtained by first difluoroacetonitrile of the formula (II) in a first step by catalytic hydrogenation to N (2,2-difluoroethyl) amide of the formula (III ) and then reacting the thus obtained N (2,2-difluoroethyl) amide by treatment with acid to 2,2-difluoroethylamine.
  • the reaction is shown in the following reaction scheme, wherein R 1 may have the meanings given below.
  • the present invention thus relates to a process for the preparation of 2,2-difluoroethylamine of the formula (I) comprising the following reaction steps
  • R 1 is H, Ci_i 2 alkyl, C 3-8 cycloalkyl, Ci_i 2 haloalkyl, aryl (eg, phenyl), Ci_i 2 -alkyl-C 6 _i 0 is aryl, R 1 is preferably H, methyl , Trifluoromethyl, ethyl, n-propyl, isopropyl, n-butyl, iso-butyl, sec-butyl, and t-butyl, n-pentyl, n-hexyl, 1, 3-dimethylbutyl, 3,3-dimethylbutyl , n-heptyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, phenyl or benzyl, more preferably H, methyl, t-butyl or phenyl. in the presence of an organic acid of general formula (IV
  • R 1 has the abovementioned meaning, preferably in the presence of CF 3 COOH, CH 3 COOH, CH 3 COCl, benzoyl chloride, acetic anhydride, pivaloic anhydride, t-butyl acetic anhydride, trifluoroacetic anhydride or benzoyl anhydride or mixtures thereof, particularly preferably in the presence of CH 3 COOH, CH 3 COCl or acetic anhydride or mixtures thereof; and
  • the invention further relates to the difluoroethyl amide intermediate of general formula (III) obtained by the process of the invention as defined above.
  • step (a) takes place in the presence of a catalyst, wherein gaseous hydrogen is introduced into the reaction vessel or generated in situ in the reaction vessel by the use of formic acid or hydrazine and their derivatives or salts thereof.
  • catalyst for the catalytic hydrogenation according to the invention in reaction step (a), it is possible to use as catalyst any catalyst known to the person skilled in the art suitable for catalytic hydrogenation.
  • palladium catalysts platinum catalysts, Raney nickel catalysts, Lindlar catalysts, ruthenium and rhodium catalysts are suitable.
  • Suitable catalysts preferably contain one or more metals of groups 8-10 of the Periodic Table, in particular one or more metals selected from iron, ruthenium, osmium, cobalt, rhodium, iridium, nickel, palladium and platinum.
  • the metals may be in any chemical form, eg, elemental, colloidal, as salts or oxides, together with complexing agents as chelates, or as alloys, which alloys may include other metals, such as aluminum, in addition to the metals listed above.
  • the metals may be present in supported form, ie on any, preferably inorganic, support. Suitable supports are, for example, carbon (carbon or activated carbon), aluminum oxide, silicon dioxide, zirconium dioxide or titanium dioxide.
  • Preferred catalysts according to the invention contain one or more metals of groups 8-10 of the periodic table on an inorganic support. Particularly preferred according to the invention are catalysts which comprise platinum and / or palladium and are optionally applied to an inorganic support. Such catalysts include PtO 2 , Pd (OH) 2 on activated carbon (Pearlman catalyst), Raney nickel, and Lindlar catalysts.
  • the catalyst based on the difluoroacetonitrile used, in a concentration of about 0.01 to about 30 wt .-% is used.
  • the catalyst is in a concentration of about 0.1 to about 12 wt .-% used, particularly preferably from about 0.1 to about 2 wt .-%.
  • step (a) of the process according to the invention usually in a first step (i) difluoroacetonitrile and the catalyst with the organic acid, acid chloride, acid anhydride or mixtures thereof are introduced and in a second step (ii) hydrogen is introduced or generated in situ.
  • steps (i) and (ii) is possible. It is also possible to hydrogenate continuously or batchwise (batchwise or batchwise).
  • the catalytic hydrogenation may be carried out under overpressure (i.e., up to about 200 bar) in an autoclave or at atmospheric pressure in a hydrogen gas atmosphere. Especially at high reaction temperatures, it may be helpful to work at elevated pressure.
  • the (additional) pressure increase can be effected by supplying an inert gas, such as nitrogen or argon.
  • the hydrogenation according to the invention is preferably carried out at a pressure in the range of about 1 to about 100 bar, more preferably at a pressure in the range of about 5 to about 25 bar.
  • reaction step (a) The organic acid, acid chloride or acid anhydride or mixtures thereof present in reaction step (a) lead to the fact that the difluoroethylamine formed is removed from the hydrogenation process and does not react with (CF 2 HCH 2 ) 2 NH.
  • the necessary amount of the organic acid, acid chloride or acid anhydride present in reaction step (a), based on difluoroacetonitrile, can easily be determined by a person skilled in the art by routine experiments.
  • the molar ratio of difluoroacetonitrile to the organic acid, acid chloride or acid anhydride or mixtures thereof used may be, for example, about 0.5 to 10, or about 0.9 to 2. A ratio of about 1 to 1.1 is preferred.
  • the use of larger amounts of organic acid, acid chloride or acid anhydride or mixtures thereof is possible in principle, but is disadvantageous for economic reasons.
  • Preferred reaction temperatures for the hydrogenation in reaction step (a) range from -20 ° C to 100 ° C, with temperatures of 0 ° C to 40 ° C being preferred.
  • the reaction time of the hydrogenation is generally 30 minutes to 24 hours, with shorter or longer reaction times not adversely affecting.
  • the amide of the formula (III) is reacted with a suitable acid to give 2,2-difluoroamine.
  • the amide of formula (III) can also be isolated by removing the catalyst and the solvent, if present, and feeding reaction step (b).
  • the acids usable in the reaction step (b) are selected from phosphoric acid (H 3 PO 4 ), sulfuric acid (H 2 S0 4 ), hydrochloric acid (HCl), hydrobromic acid (HBr), hydrofluoric acid (HF), potassium hydrogensulfate (KHSO 4 ), CF 3 COOH, CF 3 SO 3 H, CH 3 COOH, and p-tolylsulfonic acid.
  • Preferred reaction temperatures for the cleavage of the difluoroamide of formula (III) in reaction step (b) range from about 0 ° C to about 100 ° C.
  • solvents difluoroacetonitriles
  • the catalytic hydrogenation can also be carried out without a solvent.
  • Solvents are advantageously used in such an amount that the reaction mixture remains easy to stir throughout the process. It is advantageous to use, based on the difluoroacetonitrile used, 1 to 50 times the amount of solvent, preferably 2 to 40 times the amount of solvent, more preferably 2 to 30 times the amount of solvent.
  • Suitable solvents for carrying out the process according to the invention are all organic solvents which are inert under the reaction conditions, the type of solvent used being of the type of reaction, in particular of the type of catalyst used and / or the source of hydrogen (introduction of gaseous hydrogen or in situ Generation). Solvents according to the invention are understood as meaning mixtures of pure solvents.
  • ethers such as ethyl propyl ether, n-butyl ether, anisole, phenetole, cyclohexyl methyl ether, dimethyl ether, diethyl ether, dimethyl glycol diphenyl ether, dipropl ether, diisopropyl ether, di-n-butyl ether, diisobutyl ether, diisoamyl ether, ethylene glycol dimethyl ether, isopropyl ethyl ether, methyl tert-butyl ether , Tetrahydrofuran, methyl tetrahydrofuran, dioxane, dichloro diethyl ether and polyethers of ethylene oxide and / or propylene oxide; aliphatic, cycloaliphatic or aromatic hydrocarbons such as pentane, hexane, heptane, octane, nonane and technical
  • ethers such as eth
  • Organic acids such as formic acid or acetic acid.
  • water can also be used.
  • the organic acid, acid chloride or anhydride present in the reaction, and mixtures thereof may also be used as the solvent.
  • Preferred solvents according to the invention in the reaction step (a) are toluene, tetrahydrofuran, methyl tetrahydrofuran or mixtures thereof.
  • reaction step (b) water is preferred as the solvent according to the invention.
  • the work-up and purification can be carried out via the free amine or via its salts. If the 2,2-difluoroethylamine is freely present by the process according to the invention, it is, if necessary, purified by distillation. If 2,2-difluoroethylamine is in the form of a salt, the purification is carried out if necessary, preferably by crystallization.
  • Preferred salts are, for example, sulfates, hydrochlorides or acetates.
  • Water-soluble salts of 2,2-difluoroethylamine are generally purified by extraction from an aqueous solution.
  • the free 2,2-difluoroethylamine is liberated by reacting the corresponding salt with organic or inorganic bases (eg NaHCC> 3 , Na 2 C0 3 or NaOH).
  • organic or inorganic bases eg NaHCC> 3 , Na 2 C0 3 or NaOH.
  • the difluoroethylamine is distilled off directly from the aqueous solution or extracted into an organic solvent.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Catalysts (AREA)

Abstract

La présente invention concerne un procédé de production de 2,2-difluoréthylamine de formule (I) et de ses sels, tels que, par exemple, les sulfates, chlorhydrates ou acétates, à partir du difluoracétonitrile.
PCT/EP2010/069036 2009-12-11 2010-12-07 Procédé de production de 2,2-difluoréthylamine et de ses sels à partir de difluoracétonitrile Ceased WO2011069994A1 (fr)

Priority Applications (10)

Application Number Priority Date Filing Date Title
BR112012014046-9A BR112012014046A2 (pt) 2009-12-11 2010-12-07 processo para a produção de 2,2-difluoroetilamina e de seus sais a partir de difluoroacetonitrila
ES10798990.7T ES2524304T3 (es) 2009-12-11 2010-12-07 Procedimiento para la preparación de 2,2-difluoroetilamina, así como de sus sales, partiendo de difluoroacetonitrilo
JP2012542506A JP5734997B2 (ja) 2009-12-11 2010-12-07 ジフルオロアセトンニトリルから出発して２，２−ジフルオロエチルアミン及びその塩を調製する方法
CN201080055886.XA CN102741218B (zh) 2009-12-11 2010-12-07 由二氟乙腈制备2,2-二氟乙胺及其盐的方法
IN5122DEN2012 IN2012DN05122A (fr) 2009-12-11 2010-12-07
EP10798990.7A EP2509937B1 (fr) 2009-12-11 2010-12-07 Procédé de production de 2,2-difluoréthylamine et de ses sels à partir de difluoracétonitrile
KR1020127017811A KR101788083B1 (ko) 2009-12-11 2010-12-07 디플루오로아세토니트릴로부터 2,2-디플루오로에틸아민 및 그의 염을 제조하는 방법
DK10798990.7T DK2509937T3 (en) 2009-12-11 2010-12-07 PROCEDURE FOR PREPARING 2,2-DIFLUORETHYLAMINE AND SALTS THEREOF OUT OF DIFLUORACETONITRIL
MX2012006590A MX2012006590A (es) 2009-12-11 2010-12-07 Procedimiento para la preparacion de 2,2-difluoroetilamina, asi como de sus sales, partiendo de difluoroacetonitrilo.
IL219711A IL219711A (en) 2009-12-11 2012-05-10 Process for making 2, 2 - diplooroethylamine and its salts from diplooroacetonitrile

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
EP09178860 2009-12-11
EP09178860.4 2009-12-11
US28660709P 2009-12-15 2009-12-15
US61/286,607 2009-12-15

Publications (1)

Publication Number Publication Date
WO2011069994A1 true WO2011069994A1 (fr) 2011-06-16

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PCT/EP2010/069036 Ceased WO2011069994A1 (fr) 2009-12-11 2010-12-07 Procédé de production de 2,2-difluoréthylamine et de ses sels à partir de difluoracétonitrile

Country Status (12)

Country Link
US (1) US8242311B2 (fr)
EP (1) EP2509937B1 (fr)
JP (1) JP5734997B2 (fr)
KR (1) KR101788083B1 (fr)
CN (1) CN102741218B (fr)
DK (1) DK2509937T3 (fr)
ES (1) ES2524304T3 (fr)
IL (1) IL219711A (fr)
IN (1) IN2012DN05122A (fr)
MX (1) MX2012006590A (fr)
TW (1) TWI482749B (fr)
WO (1) WO2011069994A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2016023773A1 (fr) * 2014-08-12 2016-02-18 Basf Se Procédé de préparation de 2,2-difluoroéthylamine
WO2022175132A1 (fr) 2021-02-17 2022-08-25 Bayer Aktiengesellschaft Procédé de préparation de polyfluoroalkylamines à partir de polyfluoroalkylalcools
CN117430492A (zh) * 2023-12-20 2024-01-23 山东国邦药业有限公司 一种二氟乙酸的制备方法

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2972452B1 (fr) * 2011-03-09 2013-03-15 Rhodia Operations Procede de preparation du difluoroacetonitrile et de ses derives
TWI565686B (zh) * 2015-11-26 2017-01-11 南亞塑膠工業股份有限公司 一種ｎ，ｎ’－雙（３－胺基丙基）－１，２－乙二胺的製備方法
EP3841154B1 (fr) * 2018-08-24 2022-09-21 Dow Silicones Corporation Procédé de polymérisation par condensation de polydiorganosiloxanes à terminaison hydroxyle

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US20090062251A1 (en) * 2007-08-17 2009-03-05 Astrazeneca Ab Novel Compounds 002
ES2438568T3 (es) * 2007-09-18 2014-01-17 Bayer Cropscience Ag Procedimiento para la preparación de derivados de 2,2-difluoroetilamina mediante hidrogenación de amida

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US4030994A (en) * 1971-06-18 1977-06-21 Merck & Co., Inc. Substitutive fluorination of organic compounds

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DONETTI A ET AL: "N-(fluoroethyl)(imidazolylphenyl)formamidines. The issue of the active species of mifentidine.", JOURNAL OF MEDICINAL CHEMISTRY MAY 1989, vol. 32, no. 5, May 1989 (1989-05-01), pages 957 - 961, XP002573225, ISSN: 0022-2623 *
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GRUNEWALD G L ET AL: "Application of the Goldilocks effect to the design of potent and selective inhibitors of phenylethanolamine N-methyltransferase: balancing Pka and steric effects in the optimization of 3-methyl-1,2,3,4-tetrahydroisoquinoline inhibitors by beta-fluorination", JOURNAL OF MEDICINAL CHEMISTRY, USAMERICAN CHEMICAL SOCIETY. WASHINGTON, vol. 49, no. 10, 1 January 2006 (2006-01-01), pages 2939 - 2952, XP002487200 *
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KLUGER R ET AL: "Carboxylic acid participation in amide hydrolysis. Evidence that separation of a nonbonded complex can be rate determining", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, NEW YORK, USA, vol. 104, no. 10, 1 January 1982 (1982-01-01), pages 2891 - 2897, XP002504652, ISSN: 0002-7863 *
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WODZINSKA J ET AL: "pKa-dependent formation of amides in water from an acyl phosphate monoester and amines", JOURNAL OF ORGANIC CHEMISTRY 20080620 AMERICAN CHEMICAL SOCIETY US, vol. 73, no. 12, 20 June 2008 (2008-06-20), pages 4753 - 4754, XP002573226 *

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2016023773A1 (fr) * 2014-08-12 2016-02-18 Basf Se Procédé de préparation de 2,2-difluoroéthylamine
WO2022175132A1 (fr) 2021-02-17 2022-08-25 Bayer Aktiengesellschaft Procédé de préparation de polyfluoroalkylamines à partir de polyfluoroalkylalcools
CN117430492A (zh) * 2023-12-20 2024-01-23 山东国邦药业有限公司 一种二氟乙酸的制备方法
CN117430492B (zh) * 2023-12-20 2024-03-22 山东国邦药业有限公司 一种二氟乙酸的制备方法

Also Published As

Publication number Publication date
ES2524304T3 (es) 2014-12-05
DK2509937T3 (en) 2014-12-15
CN102741218A (zh) 2012-10-17
MX2012006590A (es) 2012-10-03
IN2012DN05122A (fr) 2015-10-23
US20110166388A1 (en) 2011-07-07
EP2509937A1 (fr) 2012-10-17
KR20120092698A (ko) 2012-08-21
TWI482749B (zh) 2015-05-01
EP2509937B1 (fr) 2014-10-08
CN102741218B (zh) 2014-05-07
JP5734997B2 (ja) 2015-06-17
IL219711A0 (en) 2012-07-31
KR101788083B1 (ko) 2017-10-19
US8242311B2 (en) 2012-08-14
JP2013513566A (ja) 2013-04-22
TW201130787A (en) 2011-09-16
IL219711A (en) 2014-07-31

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