WO2008038637A1 - Procédé de production d'amines libres - Google Patents

Procédé de production d'amines libres Download PDF

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Publication number
WO2008038637A1
WO2008038637A1 PCT/JP2007/068583 JP2007068583W WO2008038637A1 WO 2008038637 A1 WO2008038637 A1 WO 2008038637A1 JP 2007068583 W JP2007068583 W JP 2007068583W WO 2008038637 A1 WO2008038637 A1 WO 2008038637A1
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WO
WIPO (PCT)
Prior art keywords
acid
amine
amino
salt
ethylenediamine
Prior art date
Application number
PCT/JP2007/068583
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English (en)
Japanese (ja)
Inventor
Akira Nishiyama
Original Assignee
Kaneka Corporation
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
Application filed by Kaneka Corporation filed Critical Kaneka Corporation
Priority to JP2008536378A priority Critical patent/JP5254799B2/ja
Publication of WO2008038637A1 publication Critical patent/WO2008038637A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/06—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with radicals, containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C213/08—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions not involving the formation of amino groups, hydroxy groups or etherified or esterified hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/12—Oxygen or sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/14—Nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D211/26—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D211/56—Nitrogen atoms

Definitions

  • the present invention relates to a method for producing free amines, which obtains various amines useful as synthetic intermediates for pharmaceuticals and agricultural chemicals as free products.
  • a method of forming a salt from an amine and an acid and crystallization from an organic solvent is often used. Further, this method can be applied to form a salt from a racemic amine and an optically active acid, and precipitate the salt of one enantiomer as a crystal for optical desorption. Examples of a method for liberating an amine from a salt of an amine and an acid thus obtained include the following methods.
  • a salt of an amine and an acid is dissolved in water and neutralized by adding an alkali such as sodium hydroxide or potassium carbonate, and then an organic solvent such as ethyl acetate, toluene, or methylene chloride is added.
  • an organic solvent such as ethyl acetate, toluene, or methylene chloride.
  • (S) -1 monobenzyl 3-amino pyrrolidine and dibenzoyl L tartaric acid are dissolved in an aqueous sodium hydroxide solution to separate the free amine, and the aqueous layer is further separated into toluene.
  • a salt of an amine and an acid is dissolved or suspended in an alcohol solvent such as methanol or ethanol.
  • a base such as sodium methoxide or sodium ethoxide is added for neutralization, and the precipitated inorganic salt is removed by filtration, and then an alcohol solution of free amine is obtained as a filtrate.
  • free amine is obtained by concentrating or separating the amine and alcohol by distillation. Specifically, for example, (S) -3-amaminopyrrolidine dihydrochloride is added to a methanol solution of 28% sodium methoxide, the precipitated inorganic salt is filtered off, and the filtrate is concentrated at normal pressure. Further, the concentrated solution was distilled at atmospheric pressure to obtain liberated (S) -3-aminopyrrolidine.
  • Patent Document 3 % (Patent Document 3).
  • Patent Document 1 Japanese Patent Laid-Open No. 9 176115
  • Patent Document 2 JP-A-1 294633
  • Patent Document 3 JP-A-2-218664
  • Non-Patent Document 1 Org. Synth., V, 273 (1973).
  • the present invention includes a step of adding an amino alcohol or a polyamine to a salt of an amine and an acid having 1 to 10 carbon atoms which may have a substituent, and performing distillation.
  • the present invention also relates to a method for producing the free form of ammine.
  • the present invention is characterized in that an amino alcohol or a polyamine is added to a salt of an amine and an acid having 1 to 10 carbon atoms which may have a substituent, and distilled.
  • the present invention relates to a method for obtaining a free form of ammine.
  • an organic solvent is not required for obtaining a free amine from a salt of an amine and an acid.
  • wasteful energy is not consumed by reducing complicated concentration and filtration operations as much as possible.
  • it is a simple and versatile method. Therefore, free amine can be obtained easily and efficiently at low cost.
  • a free amine is obtained by adding an amino alcohol or a polyamine to a salt of an amine and an acid having 1 to 10 carbon atoms, which may have a substituent, and performing distillation. . It is not necessary to perform an extraction operation, a concentration operation, or a filtration operation by adding an amino alcohol or a polyamine to a salt of an amine and an acid and performing a direct distillation operation.
  • the amine having 1 to 10 carbon atoms which may have the substituent is not particularly limited, and may be any of a chain amine and a cyclic amine.
  • the substituent is not particularly limited as long as it is thermally stable and inactive with respect to amine.
  • it is an amine having a boiling point of 250 ° C. or less at normal pressure, more preferably 200 ° C. or less at normal pressure.
  • any material that can be vaporized under reduced pressure is included in the present invention.
  • amine having 1 to 10 carbon atoms which may have the substituent include 2-amino 1-propanol, 1-amino-2-propanol, 2-amino-1-butanol, and 1-dimethylamine.
  • Examples include piperidine, 1 (2 pyrrolidinylmethyl) pyrrolidine, 3 quinuclidinol, and tetrahydrofurfurylamine. These may be optically active substances.
  • it is 2 amino-1-butanol, 2 methylpyrrolidine, 2 methylbiperidine, 3-aminopyrrolidine, 3-aminobiperidine, or 3-pyrrolidinol, more preferably (S) -2-amino-1-butanol, (S) — 2-Methylpyrrolidine, (S) — 2-Methylbiperidine, (S) — 3-Aminopyrrolidine, (S) — 3-Aminobiperidine, (S) — 3-Pyrrolidinol, (R) — 2-Amino- 1-butanol, (R) -2-methylpyrrolidine, (R) -2-methinorepiperidine, (R) -3-aminopyrrolidine, (R) -3-aminobiperidine, or (R) -3-pyrrolidinol is there. Particularly preferred is (S) -3-amino pyrrolidine or (R) -3-amino
  • the acid in the salt of an amine having 1 to 10 carbon atoms which may have a substituent is not particularly limited, but specifically, for example, hydrogen fluoride, hydrogen chloride, odor Inorganic acids such as hydrogen iodide, hydrogen iodide, sulfuric acid, nitric acid, phosphoric acid, boric acid; formic acid, acetic acid, propionic acid, butyric acid, isobutyric acid, pivalic acid, cyclohexane carboxylic acid, cycloacetic acid, dichloroacetic acid, trichloro Oral acetic acid, trifluoroacetic acid, acrylic acid, fumaric acid, maleic acid, benzoic acid, phthalic acid, oxalic acid, malonic acid, citrate, L tartaric acid, D tartaric acid, dibenzoyl L tartaric acid, diben Zoinole D-tartaric acid, di-p-toluoyl L-tartaric acid, di-
  • a sulfonic acid is mentioned.
  • the salt of an amine having 1 to 10 carbon atoms that may have the above-mentioned substituent and an acid its production method is not particularly limited, but specifically, for example, an amino group of the amine. Is protected with a protecting group such as acetyl group, benzoyl group, phthaloyl group, methoxycarbonyl group, ethoxycarbonyl group, tert butoxycarbonyl group, or benzyloxycarbonyl group, for example, hydrogen fluoride, hydrogen chloride, odor Inorganic acids such as hydrogen iodide, hydrogen iodide, sulfuric acid, nitric acid, phosphoric acid, boric acid; methanesulfonic acid, ethanesulfonic acid, trifluoromethanesulfonic acid, benzenesulfonic acid, p toluenesulfonic acid, p Deprotection with an acid such as acid, m sulfonic acid
  • Salts may be prepared with acids. Further, for the purpose of improving the purity of the amine, it may be produced by forming a salt with the acid and precipitating it as a crystal from a solvent.
  • the racemic amines can be added to L-tartaric acid, D tartaric acid, dibenzoyl L, tartaric acid, dibenzoyl D It may be a salt of an optically active amine and an optically active acid formed by diastereomer salt formation with an optically active carboxylic acid such as L mandelic acid and D mandelic acid.
  • the amino alcohols or polyamines added to this system may have a boiling point higher than that of the amine having 1 to 10 carbon atoms which may have the above substituents! /. Preferably, it may have a substituent! /, A boiling point of an amine alcohol or polyamine to be added is higher than the boiling point of an amine having 1 to 10 carbon atoms; Furthermore, the amino alcohols or poly Amines need to be sufficiently polar to dissolve the salt of the amine and acid.
  • the amino alcohols or polyamines are not particularly limited. Specifically, for example, 1-amino-2-butanol, 2 amino-1-butanol, 4 amino-1-butanol, 2-aminocyclohexanol, 4 amino-1 -Jetylaminopentane, 3-amino 2,2-dimethyl-1-propanol, 2-aminoethanol, 2- (2-aminoethoxy) ethanol, 2- (2-aminoethylamino) ethanol, N- (2 —Aminoethyl) aniline, N— (2-aminoethinole) morpholine, N— (2-aminoethinole) piperazine, 1 (2-aminoethyl) piperidine, 2 amino-2-ethynole 1,3 propanediol, 1 -(2 aminoethyl) pyrrolidine, 4 amino-2 methyl-1-butanol, 4- (aminomethyl) piperidine, 2 amino-2 methin
  • the target amine In order to release the target amine more efficiently, it is also derived from the structure of the amine, but as the amino alcohol or polyamine to be added, an aliphatic amine is preferable to an aromatic amine. Also, secondary amines are preferred over tertiary amines. Primary amines are even more preferred than secondary amines. In addition, polyamines such as triamine and tetramine, which are preferred to diamines over monoamino alcohols, are more preferred. As diamines, those having an amino group on the adjacent carbon are preferable.
  • liquids at 30 ° C are preferred from the viewpoint of ease of handling, for example, 2- (2-aminoethylamino) ethanol, N- (2-aminoethyl) morpholine, N- (2-amino Ethyl) piperazine, 1- (2-aminoethyl) piperidine, 1- (2-aminoethyl) pyrrolidine, N, N, 1-bis (3-aminopropyl) ethylenediamine, 1,4-bis (3-aminopropyl) pipera Gin, N—n Butynoleethylenediamine, 1,2-Cyclohexanediamine, 1,2-Diamino 2-methylpropane, N, N′-Dethylethylenediamine, N, N Diisopropylethylenediamine, N , N, Dimethinolepiperazine, N Ethinorepiperazine, Homopiperazine, N— (2 Hydroxypropinole) ethylenediamine,
  • the amount of the amino alcohol or polyamine used may be set according to the number of amino groups contained in the amino alcohol or polyamine. If there is a single amino group, it should be used in an amount of 1 molar amount or more with respect to the salt of the amine and the acid. Is an amino group of polyamines (n represents a positive integer), 1 / n times the molar amount, preferably 1. It is preferable to use 3 / n times the molar amount or more, more preferably 1.5 / n times the molar amount or more.
  • the amine and the acid are used. If the salt is used in an amount of 0.34 times the molar amount or more and 4 amino groups are used, the amount of 0.25 times the molar amount or more of the salt of the amine and the acid may be used.
  • the amino alcohol or polyamine is preferably added in an amount of m / n-fold molar amount or more. It is preferable to use 1 ⁇ 3 m / n-fold molar amount or more, more preferably 1.5 ⁇ 5 m / n-fold molar amount or more. For example, if there are two protons such as oxalic acid, m becomes 2.
  • the upper limit of the amount of the amino alcohol or polyamine used is not particularly limited. However, from the viewpoint of economy, the salt of the amine and the acid is preferably used as long as the amino compound to be added has one amino group. When the amount of amino group is 5 or less, and the number of amino groups is one, the number of amino groups to be added may be 1 / n times that of one amino group (n is the same as above). Of course, when the acid in the salt of amine and acid has m protons (m is the same as above), the upper limit of the amount of aminoamino or polyamine having n amino groups is (5m) A molar amount of / n is preferred.
  • amino alcohols or polyamines it is preferable to start distillation after adding the amino alcohols or polyamines to the salt of the amine and the acid. Further, aminoanols or polyamines may be further added after the start of distillation.
  • the distillation method of the present invention may be either atmospheric pressure distillation or reduced pressure distillation.
  • Amines obtained by distillation contain acids, and may contain amino alcohols or polyamines in some cases. In this case, re-distillation should be performed to increase the purity of the target amine.
  • the filtrate was concentrated under normal pressure heating (external temperature: 110 ° C., internal temperature: ⁇ 85 ° C.) to obtain a yellow liquid as a residue.
  • 50 mL of tetrahydrofuran concentrated again under normal pressure heating (external temperature: 110 ° C, internal temperature: ⁇ 85 ° C), and the residue was distilled at atmospheric pressure, so that the external temperature: ⁇ 180 ° C.
  • this liquid was distilled under reduced pressure.
  • 3.5491 g of a colorless liquid was obtained at an outlet temperature of 133 ° C.
  • the amount of (R) -3 pyrrolidinol of this liquid was measured, the content was 78.8% by weight, which was 64% in terms of recovery.

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

Abstract

La présente invention concerne un procédé propre, simple et polyvalent destiné à produire une amine libre à partir d'un sel d'amine possédant de 1 à 10 atomes de carbone, qui peut avoir un substituant comprenant un acide, qui ne nécessite pas l'utilisation de l'eau ou de solvant organique et qui est réduit au maximum lors d'opérations compliquées et ne consomme donc pas plus d'énergie que nécessaire. L'invention porte spécifiquement sur un procédé simple et polyvalent qui comprend les étapes consistant à ajouter un aminoalcool ou une polyamine à un sel d'amine possédant de 1 à 10 atomes de carbone, qui peut avoir un substituant comprenant un acide, et à distiller le mélange, ce qui produit une forme libre d'amine possédant de 1 à 10 atomes de carbone pouvant renfermer le substituant.
PCT/JP2007/068583 2006-09-26 2007-09-25 Procédé de production d'amines libres WO2008038637A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP2008536378A JP5254799B2 (ja) 2006-09-26 2007-09-25 遊離アミンの製造方法

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JP2006261108 2006-09-26
JP2006-261108 2006-09-26

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WO2008038637A1 true WO2008038637A1 (fr) 2008-04-03

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013058241A1 (fr) * 2011-10-18 2013-04-25 株式会社カネカ Procédé de production de (r)-2-amino-éthylhexanol

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2000026381A (ja) * 1998-07-13 2000-01-25 Sumika Chemical Analysis Service Ltd アミノアルコールの単離方法
WO2004089872A1 (fr) * 2003-04-08 2004-10-21 Schwarz Pharma Ag Bases de grande pureté de monoesters de 3,3-diphénylpropylamine

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2000026381A (ja) * 1998-07-13 2000-01-25 Sumika Chemical Analysis Service Ltd アミノアルコールの単離方法
WO2004089872A1 (fr) * 2003-04-08 2004-10-21 Schwarz Pharma Ag Bases de grande pureté de monoesters de 3,3-diphénylpropylamine

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013058241A1 (fr) * 2011-10-18 2013-04-25 株式会社カネカ Procédé de production de (r)-2-amino-éthylhexanol

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JPWO2008038637A1 (ja) 2010-01-28

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