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WO2004087637A1 - Production de composes de n-alkylamide - Google Patents

Production de composes de n-alkylamide Download PDF

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Publication number
WO2004087637A1
WO2004087637A1 PCT/JP2004/004561 JP2004004561W WO2004087637A1 WO 2004087637 A1 WO2004087637 A1 WO 2004087637A1 JP 2004004561 W JP2004004561 W JP 2004004561W WO 2004087637 A1 WO2004087637 A1 WO 2004087637A1
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Prior art keywords
formula
group
substituted
alkyl group
compounds
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PCT/JP2004/004561
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English (en)
Inventor
Takaji Matsumoto
Tsukasa Sotoguchi
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Takasago International Corp
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Takasago International Corp
Takasago Perfumery Industry Co
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Publication of WO2004087637A1 publication Critical patent/WO2004087637A1/fr
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/08—Preparation of carboxylic acid amides from amides by reaction at nitrogen atoms of carboxamide groups

Definitions

  • the present invention relates to a process for producing an N-alkylamide compound useful, for example, as intermediates for the synthesis of pharmaceuticals, agro ⁇ hemicals , etc.
  • N-acylaniline derivatives have been widely used as a therapeutic agent for insomnia, etc.
  • Patent Reference 1 discloses a method which comprises reacting m- acetamidoacetophenone compounds with either methyl iodide or dimethyl sulfate in the presence of phase transfer catalyst and sodium hydride or aqueous sodium hydroxide solution.
  • the method described in the Patent Reference 1 has a drawback of giving by-products which are formed by methylation on the acetyl groups of m-acetamidoacetophenone compounds and are isolated from the objective compound with difficulty, requiring an additional process for separating the desired m- (N-methylacetamido)acetophenone compounds and said by-products, which makes the operation rather complicated.
  • the method requires a phase transfer catalyst because of two phase reaction using dimethyl sulfate and aqueous sodium hydroxide solution.
  • a process which makes it possible to selectively methylate the amide group on the nitrogen atom and gives the desired m- (N-methyla ⁇ etamido)acetophenone in a good yield has been desired eagerly.
  • Patent Reference 1 WO01/10868
  • the present invention has been worked out in the light of the problem mentioned above and the aim of the present invention is to provide a process which makes it possible to selectively alkylate the amide groups on their nitrogen atom, giving the desired N-acylaniline derivatives in good yields .
  • the present invention is as follows: 1) A process for producing an N-alkylamide compound of the formula ( 3 ) :
  • R 1 and R 2 are each independently an alkyl group, a substituted alkyl group, an alkenyl group, a substituted alkenyl group, an aryl group or a substituted aryl group and R 3 is an alkyl group
  • R 1 and R 2 are each independently an alkyl group, a substituted alkyl group, an alkenyl group, a substituted alkenyl group, an aryl group or a substituted aryl group and R 3 is an alkyl group
  • R 1 and R 2 are each independently an alkyl group, a substituted alkyl group, an alkenyl group, a substituted alkenyl group, an aryl group or a substituted aryl group, and R 3 is an alkyl group
  • R 1 and R 2 are each independently an alkyl group, a substituted alkyl group, an alkenyl group, a substituted alkenyl group, an aryl group or a substituted aryl group, and R 3 is an alkyl group
  • R 1 and R 2 are each independently an alkyl group, a substituted alkyl group, an alkenyl group, a substituted alkenyl group, an aryl group or a substituted aryl group
  • the compounds of the formula (3) are those of the formula (3a) :
  • R 3 is an alkyl group, and R 1 and R 2 have each the same meaning as described above.
  • R 1 is an alkyl group, a substituted alkyl group, an alkenyl group, a substituted alkenyl group, an aryl group or a substituted aryl group
  • the compounds of the formula (2) are those of the formula (2a):
  • R 1 and R 2 are each independently an alkyl group, a substituted alkyl group, an alkenyl group, a substituted alkenyl group, an aryl group or a substituted aryl group
  • the compounds of the formula (3) are those of the formula (3a) :
  • R 3 is an alley1 group, and R 1 and R a have each the same meaning as described above.
  • Alkyl groups represented by R 1 and R 2 include linear, branched, or cyclic alkyl groups of, for example, 1 to 6 carbon atoms. Specific examples of such alkyl groups include methyl, ethyl, n-propyl, 2-propyl, n-butyl, 2-butyl, isobutyl, tert-butyl, n-pentyl, 2-pentyl, 2-methylbutyl, 3- methylbutyl, 2, 2-dimethylpropyl, n-hexyl, 2-hexyl, 3-hexyl, 2-methylpent n-2-yl, 3-methylpentan-3-yl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 2-methylpentan-3-yl, cyclohexyl, etc. Among them, the alkyl groups of 1 to 3 carbon atoms are preferable.
  • Alkenyl groups include linear or branched alkenyl groups of, for example, 2 to 6 carbon atoms. Specific examples of such alkenyl groups include vinyl, propenyl, 1- butenyl, 2-butenyl, pentenyl, hexenyl, etc.
  • Aryl groups include aryl groups of, for example, 6 to 14 carbon atoms, and specific examples of the aryl groups include a phenyl group and a naphthyl group.
  • Substituted alkyl groups include those alkyl groups mentioned above, at least one hydrogen atom of which is substituted by a substituent such as alkoxy, halogen, cyano, acyl, substituted amino, etc.
  • Alkoxy groups include linear, branched or cyclic alkoxy groups of, for example 1 to 6 carbon atoms .
  • alkoxy groups include methoxy, ethoxy, n-propoxy, 2-propoxy, n-butoxy, 2-butoxy, isobutoxy, tert-butoxy, n-pentyloxy, 2-methylbutoxy, 3- methylbutoxy, 2, 2-dimethylpropyloxy, n-hexyloxy, 2- methylpentyloxy, 3-meth ⁇ lpentyloxy, 4-methylpentyloxy, 5- methylpentyloxy, cyclohexyloxy, etc.
  • Halogen include fluorine, chlorine, bromine, iodine, etc.
  • Acyl groups include linear or branched acyl groups of, for example, 1 to 18 carbon atoms derived from carboxylic acids such as aliphatic carboxylic acids , aromatic carboxylic acids, etc.
  • Specific examples of the acyl groups include formyl, acetyl, propionyl, butyryl, pivaloyl, pentanoyl, hexanoyl, lauroyl, stearoyl, benzoyl, etc.
  • Substituted amino groups include amino groups, two hydrogen atoms of which are replaced by two alkyl groups . Specific examples of such substituted amino groups include
  • substituted alkenyl groups e.g. the substituted vinyl group
  • substituents in the substituted alkenyl groups include the same ones as described above
  • Substituted aryl groups include the same aryl groups as mentioned above, either, at least one hydrogen atom on which is replaced by substituent groups such as alkyl groups , halogenated alkyl groups , alkoxy groups , halogens , acyl groups, substituted amino groups, etc., or, two adjacent hydrogen atoms on which are replaced by an alkylenedioxy group (for example, alkylenedioxy ' groups of 1 to 3 carbon atoms, including, more specifically, a methylenedioxy group, an ethylenedioxy group, a propylenedioxy group), wherein the alkyl groups, alkoxy groups, halogens, acyl groups and substituted amino groups are the same as described above.
  • substituent groups such as alkyl groups , halogenated alkyl groups , alkoxy groups , halogens , acyl groups, substituted amino groups, etc.
  • Halogenated alkyl groups include the halogenated alkyl groups of 1 to 3 carbon atoms derived from the same alkyl group as mentioned above, at least one hydrogen atom of which is halogenated (e.g. fluorinated, chlorinated, brominated or iodinated) with halogen(s) (e.g., fluorine, chlorine, bromine or iodine).
  • halogenated e.g. fluorinated, chlorinated, brominated or iodinated
  • halogen(s) e.g., fluorine, chlorine, bromine or iodine
  • halogenated alkyl groups include chloromethyl, bromomethyl, 2-chloroethyl, 3-bromopropyl, fluoromethyl, fluoroethyl, fluoropropyl, difluoromethyl, difluoroethyl, trichloromethyl, trifluoromethyl, 2,2,2-trifluoroethyl, 3, 3, 3-trifluoropropyl, pentafluoroethyl, perfluoro-n-propyl, perfluoroisopropyl, etc.
  • aryl groups substituted by alkyl group(s) include tolyl, xylyl, etc.
  • the alkyl groups represented by R 3 include linear or branched alkyl groups of 1 to 3 carbon atoms , and the specific examples of such alkyl groups include methyl, ethyl, n-propyl, 2-propyl, etc. Among them, methyl or ethyl is preferable.
  • acylanilines represented by the formula (1) above and used in the present invention include 3 ' -aminoacetophenone, 3-propionylaniline, 3- butyrylaniline, 2 ' -aminoacetophenone, 2-propionylaniline, 2-butyrylaniline, 4 ' -aminoacetophenone, 4-propionylaniline, 4-butyrylaniline.
  • amide compounds represented by the formula (2) above include N-(3- acetylphenyl)acetamide, N- ( 3-propionylphenyl)acetamide, N- ( 3-butyrylphenyl)acetamide, N- (2-acetylphenyl)acetamide, N- ( 2-propionylphenyl)acetamide, N- ( 2-butyrylphenyl)acetamide, N- (4-acetylphenyl)acetamide, N- ( 4-propionylphenyl)acetamide, N- (4-butyrylphenyl)acetamide, 3- (3-ethoxy-l-oxo-2- propenyl) -N-acetanilide, 3-(3-(N' ,N' -dimethylamino) -1-oxo- 2-propenyl-N-acetanilide, etc.
  • N-alkylamide compounds represented by the formula (3) above and obtainable by the process of the present invention include N-(3- acetylphenyl) -N-methylacetamide, N- (3-acetylphenyl) -N- ethyla ⁇ etamide, N- (2-acetylphenyl) -N-methylacetamide, N-(2- acetylphenyl) -N-ethylacetamide, N- ( 4-acetylphenyl) -N- methylacetamide, N-( 4-acetylphenyl) -N-ethylacetamide, 3-(3- ethoxy-l-oxo-2-propenyl) -N-methyl-N-acetanilide, 3- (3- (N' ,N' -dimethylamino) -l-oxo-2-propenyl-N-methyl-N- acetanilide, etc.
  • the amide compounds represented by the above formula (2) can be obtained by subjecting the acylanxlines represented by the above formula (1) to N-acylation.
  • the N-acylation is carried out by reacting the acylaniline represented by the formula ( 1) with an acylating agent .
  • acylating agents examples include acid chlorides such as acetyl chloride, propionyl chloride, butyryl chloride, benzoyl chloride, etc. and carboxylic acid anhydrides such as acetic anhydride, propionic anhydride, etc.
  • the amount used of the acylating agent is appropriately selected usually f om a range of about 1.0 to 2.0 equivalents, or preferably from a range of about 1.0 to 1.5 equivalents to the amount used of the acylaniline represented by the formula ( 1) .
  • the N-acylation can be alternatively carried out, instead of using the acylating agent mentioned above, by allowing to react the carboxylic acid corresponding to the acylating agent in the presence of a dehydrating agent .
  • a dehydrating agent examples of such carboxylic acids include acetic acid, propionic acid, etc.
  • the dehydrating agents include, inorganic dehydration agents such as concentrated sulfuric acid, diphosphorous pentoxide, anhydrous zinc chloride, etc., carbodiimides such as dicyclohexylcarbodixmide, diisopropylcarbodiimide, l-ethyl-3- (3- di ethylaminopropyl)carbodumide hydrochloride, etc., polyphosphoric acid, acetic anhydride, carbonyldiimxdazole and p-toluenesulfonyl chloride
  • the N-acylation can be carried out in the presence of a base, where necessary.
  • Both inorganic and organic bases can be used as the base.
  • the organic bases include triethylamine, diisopropylethylamine, N,N- dimethylaniline, piperidine, pyridine, 4- dimethylaminopyridine, 1, 5-diazabicyclo[4.3.0]non-5-ene, 1, 8-diazabicyclo[ 5. .0]undec-7- ⁇ ne, tri-n-butylamine, N- methylmorpholine, etc.
  • examples of the inorganic bases include potassium carbonate, potassium hydroxide, lithium hydroxide, sodium bicarbonate, sodium carbonate, potassium bicarbonate, sodium hydroxide, etc.
  • the amount used of the base is appropriately selected usually from a range of about 0 to 3.0 equivalents, or preferably from a range of about 0 to 2.0 equivalents to the amount of acylaniline (1) used.
  • the N-acylation can be carried out, if necessary, in the presence of a solvent .
  • the solvents used include aliphatic hydrocarbons such as pentane, hexane, heptane, octane, decane, cyclohexane, etc., aromatic hydrocarbons such as benzene, toluene, xylene, etc., halogenated hydrocarbons such as dichloromethane, 1,2- dichloroethane, chloroform, carbon tetrachloride, o- dichlorobenzene, etc., ethers such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dimethoxyethane, ethylene glycol diethyl ether, tetrahydrofuran, 1,4-dioxane, 1, 3-dioxolane, etc., esters such as methyl acetate, ethyl acetate
  • solvents may be used solely or in appropriate combination with two or more solvents.
  • the amount of the solvent used is appropriately selected usually from a range of about 2.0 to 10.0 times by volume of, or preferably from about 3.0 to 8.0 times by volume of the acylaniline (1) used.
  • the reaction temperature is appropriately selected usually from a range of about -10 to 100°C, or preferably from a range of about 0 to 80°C.
  • the reaction time is appropriately selected usually from about 30 minutes to 24 hours, or preferably from a range of about 1 hour to 8 hours .
  • Acylanilines (1) of the formula (1) which are commercially available or appropriately in-house produced, are suitable for use.
  • sulfuric acid esters examples include sulfates such as dimethyl sulfate, diethyl sulfate, diisopropyl sulfate, etc.; sulfonates such as methyl p-toluenesulfonate, ethyl p-toluenesulfonate, etc.,- etc.
  • the amount used of the sulfuric acid ester is appropriately selected usually from a range of about 1.0 to 3.0 equivalents , or preferably from a range of about 1.0 to 2.0 equivalents to the amide compound (2).
  • the solid metal hydroxide so long as it is in the form of a solid. Examples of such a solid form are granule, pellet, pearl, powder, flake, etc., preferably granule, pearl or powder.
  • the solid metal hydroxide include alkali metal hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide, etc.; alkaline earth metal hydroxides such as magnesium hydroxide, calcium hydroxide, strontium hydroxide, barium hydroxide, etc.; etc.
  • the amount used of the metal hydroxide is appropriately selected usually from a range of about 1.0 to 3.0 equivalents , or preferably from a range of about 1.0 to 2.0 equivalents to the amide compounds (2).
  • the reaction of said amide compound with said sulfuric acid ester, namely the N-alkylation, is preferably carried out in the presence of a solvent.
  • the solvents include, aliphatic hydrocarbons such as pentane, hexane, heptane, octane, decane, cyclohexane, etc., aromatic hydrocarbons such as benzene, toluene, xylene, etc., halogenated hydrocarbons such as dichloromethane, 1, 2-dichloroethane, chloroform, carbon tetrachloride, o- dichlorobenzene , etc., ethers such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dimethoxyethane, ethylene glycol diethyl ether, tetrahydrofuran, 1,4-dioxane, 1,3-dioxolane, etc., alcohol
  • the amount of the solvent used is appropriately selected usually from a range of about 2.0 to 10.0 times by volume of, or preferably from a range of about 2.0 to 8.0 times by volume of the amide compound (2) used.
  • the reaction temperature is appropriately selected usually from a range of about 0 to 100°C, or preferably from a range of about 0 to 80°C.
  • the reaction time is appropriately selected usually from a range of about 30 minutes to 24 hours, or preferably from a range of about 1 hour to 8 hours .
  • N-alkylamide compounds of the formula (3) above obtained by the process of the present invention may be appropriately subjected to treatment such as re-dissolution, concentration, chromatography, crystallization, etc.
  • N-alkylamide compounds (3) thus obtained are useful as intermediates for the synthesis of, for example, pharmaceuticals, agrochemicals , etc.
  • Example 1 The present invention will be described in more detail by referring to Examples and Comparison Examples given below, but those are not intended to limit the present invention in any way.
  • Example 1
  • the process of the present invention is characterized in that an amide compound of the formula ( 2 ) is reacted with a sulfuric acid ester in the presence of a solid metal hydroxide without phase transfer catalyst.
  • This makes it possible to selective alkylation of the amide group on the nitrogen atom, whereby the by-produced compounds alkylated at the alkyl moiety of the acyl group substituting the phenyl group or of the N-acyl group are substantially eliminated and thus the objective N-alkylamide compounds (3) are produced efficiently in good yields, which are the effect of the present invention.
  • the process of the present invention is an industrially excellent one, giving the objective N-alkylamide compounds (3) efficiently and in good yields without substantial productxon of any by- products even when the size of the production is scaled up.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne un procédé efficace de production de dérivés de N-acylaniline par alkylation sélective d'un groupe amide au niveau de l'atome d'azote. Ce procédé consiste à faire réagir un composé amide de formule (2) (dans laquelle R1 et R2 sont chacun indépendamment un groupe alkyle, un groupe alkyle substitué, un groupe alcényle, un groupe alcényle substitué, un groupe aryle ou un groupe aryle substitué) avec un ester d'acide sulfurique en présence d'un hydroxyde métallique solide afin d'obtenir un composé N-alkylamide de formule (3) (dans laquelle R3 est un groupe alkyle et R1 et R2 ont chacun la même signification que celle indiquée précédemment).
PCT/JP2004/004561 2003-03-31 2004-03-30 Production de composes de n-alkylamide Ceased WO2004087637A1 (fr)

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JP2003094369 2003-03-31

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11891382B2 (en) 2017-04-26 2024-02-06 Basilea Pharmaceutica International AG Processes for the preparation of furazanobenzimidazoles and crystalline forms thereof
ES3032946A1 (es) * 2024-01-25 2025-07-29 Consejo Superior Investigacion Procedimiento para la produccion de amidas alifaticas

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4022802A (en) * 1971-11-26 1977-05-10 Ciba-Geigy Ag Process for the manufacture of N-substituted indoles
US4734501A (en) * 1985-10-01 1988-03-29 Eli Lilly And Company N-alkylation of dihydrolysergic acid
US5965772A (en) * 1997-05-30 1999-10-12 Dibra S.P.A. Process for the preparation of 5-(acetyl(2,3-dihydroxypropyl)amino-N,N-bis(2,3-dihydroxypropyl)-2,4,6-t riiodo
WO2001010868A1 (fr) * 1999-08-10 2001-02-15 Neurocrine Biosciences, Inc. Synthese de pyrazolopyrimidines substituees

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4022802A (en) * 1971-11-26 1977-05-10 Ciba-Geigy Ag Process for the manufacture of N-substituted indoles
US4734501A (en) * 1985-10-01 1988-03-29 Eli Lilly And Company N-alkylation of dihydrolysergic acid
US5965772A (en) * 1997-05-30 1999-10-12 Dibra S.P.A. Process for the preparation of 5-(acetyl(2,3-dihydroxypropyl)amino-N,N-bis(2,3-dihydroxypropyl)-2,4,6-t riiodo
WO2001010868A1 (fr) * 1999-08-10 2001-02-15 Neurocrine Biosciences, Inc. Synthese de pyrazolopyrimidines substituees

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
ARAI S ET AL: "AMIDE ION FORMATION AND N-ALKYLATION OF AMINOANTHRAQUINONES IN THE PRESENCE OF POTASSIUM HYDROXIDE IN DIMETHYL SULFOXIDE", 1 May 1985, BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, JAPAN PUBLICATIONS TRADING CO. TOKYO, JP, PAGE(S) 1458-1463, ISSN: 0009-2673, XP002047727 *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11891382B2 (en) 2017-04-26 2024-02-06 Basilea Pharmaceutica International AG Processes for the preparation of furazanobenzimidazoles and crystalline forms thereof
ES3032946A1 (es) * 2024-01-25 2025-07-29 Consejo Superior Investigacion Procedimiento para la produccion de amidas alifaticas
WO2025158090A1 (fr) * 2024-01-25 2025-07-31 Consejo Superior De Investigaciones Científicas (Csic) Procédé de production d'amides aliphatiques

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