GB433625A - The manufacture of aminoalkylated amines - Google Patents

The manufacture of aminoalkylated amines

Info

Publication number
GB433625A
GB433625A GB531134A GB531134A GB433625A GB 433625 A GB433625 A GB 433625A GB 531134 A GB531134 A GB 531134A GB 531134 A GB531134 A GB 531134A GB 433625 A GB433625 A GB 433625A
Authority
GB
United Kingdom
Prior art keywords
alcohol
diethylaminoethanol
methoxy
aniline
sodium
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.)
Expired
Application number
GB531134A
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.)
IG Farbenindustrie AG
Original Assignee
IG Farbenindustrie 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 NL36897D priority Critical patent/NL36897C/xx
Priority to DER84867D priority patent/DE602049C/en
Application filed by IG Farbenindustrie AG filed Critical IG Farbenindustrie AG
Priority to GB531134A priority patent/GB433625A/en
Publication of GB433625A publication Critical patent/GB433625A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D213/72—Nitrogen atoms
    • C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/04—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
    • C07C209/14—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of hydroxy groups or of etherified or esterified hydroxy groups
    • C07C209/18—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of hydroxy groups or of etherified or esterified hydroxy groups with formation of amino groups bound to carbon atoms of six-membered aromatic rings or from amines having nitrogen atoms bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D215/38—Nitrogen atoms
    • C07D215/40—Nitrogen atoms attached in position 8

Landscapes

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

Abstract

N-Aminoalkyl amines are prepared by treating primary or secondary amines with aminoalcohols in the presence of an acid or basic condensing agent. Suitable acid condensing agents are phosphorus pentoxide, phosphoric acid, boron phosphate and its hydrates, zinc chloride and aluminium chloride; suitable basic condensing agents are basic compounds of the alkali and alkaline earth metals, magnesium, and aluminium. When a basic condensing agent is used, at least one of the reagents is preferably used in the form of a compound with one of the metals specified, and the amine is preferably taken as an acyl derivative. A solvent or diluent or an excess of the aminoalcohol may be present. Examples are given of the preparation of (1) N - diethylaminoethylaniline by heating aniline with b -diethylaminoethanol in the presence of phosphorus pentoxide, zinc chloride, boron phosphate, or potassium hydroxide; or by heating aniline with the sodium compound of the alcohol; or by heating formanilide or acetanilide with the alcohol in the presence of metallic sodium or magnesium oxide; or by heating acetanilide with the sodium compound of the alcohol; the same product, and also bis(N-diethylaminoethyl) aniline, are obtained by heating aniline with b -diethylaminoethanol in the presence of hydrated boron phosphate, the products being separated by acylating the secondary amine with phthalic anhydride; (2) a -diethylaminoethylaminopyridine from a -aminopyridine and b -diethylaminoethanol in the presence of phosphorus pentoxide preferably mixed with quartz sand; (3) 6-chloro-8-diethylaminoethylaminoquinoline from 6-chloro-8-aminoquinoline and b -diethylaminoethanol in the presence of phosphoric acid; (4) 6-methoxy-8-diethylaminoethylaminoquinoline from 6-methoxy-8-aminoquinoline and b -diethylaminoethanol in the presence of phosphorus pentoxide and sand; (5) 6-methoxy-8-diethylaminopropylaminoquinoline from 6-methoxy-8-aminoquinoline and g -diethylaminopropanol in the presence of phosphorus pentoxide; (6) 2-(a -diethylamino-d -pentyl)amino naphthalene from formylb -naphthylamine and the sodium compound of a -diethylamino-d -pentyl alcohol; (7) 6-methoxy - 8 - (a -diethylamino-d -pentyl)aminoquinoline from 6-methoxy-8-formylaminoquinoline and a -diethylamino-d -pentyl alcohol in the presence of sodamide; or from 6-methoxy-8-formylaminoquinoline and the calcium compound of the alcohol; or from the sodium compound of 6-methoxy-8-formylaminoquinoline and the alcohol; or from 6-methoxy-8-aminoquinoline and the aluminium or sodium compound of the alcohol; or from 6-methoxy8-acetylaminoquinoline and the sodium compound of the alcohol; or from 6-methoxy-8-aminoquinoline and the alcohol in the presence of boron phosphate or a hydrated boron phosphate; (8) N-diethylaminoethylbenzylamine from formyl benzylamine and b -diethylaminoethanol in the presence of sodium; (9) 2-(g - piperidino-b -dimethylpropyl)aminopyridine from 2-formylaminopyridine and g -piperidino-b -dimethylpropanol in the presence of sodium; (10) 4-(g -piperidino-b -dimethylpropyl)aminopyridine from 4-formylaminopyridine and g -piperidino-b -dimethylpropanol in the presence of sodium; (11) N-diethylaminododecylamine from formyldodecylamine and b -diethylaminoethanol in the presence of sodium; (12) N-(a -diethylamino-d -pentyl)aniline from acetanilide and the sodium compound of a -diethylamino-d -pentyl alcohol; (13) N-diethylaminoethylbutylamine from butylamine and b -diethylaminoethanol in the presence of zinc chloride; (14) N-(methyl)(diethylaminoethyl) aniline from methylaniline and b -diethylaminoethanol in the presence of phosphorus pentoxide; (15) 1 : 3-bis-diethylaminoethylaminobenzene from m-phenylenediamine and b -diethylaminoethanol in the presence of phosphorus pentoxide; (16) N-(n-butylaminoethyl)aniline from aniline and b -n-butylaminoethanol in the presence of phosphorus pentoxide, or from formanilide and the alcohol in the presence of sodium; in the first case, N-bis-(n-butylaminoethyl)aniline is obtained as a by-product; (17) N-phenylethylenediamine from aniline and ethanolamine in the presence of aluminium chloride. Reference is made also to the manufacture of N-aminoalkyl derivatives of aminoanthracenes and aminoacridines.
GB531134A 1932-05-10 1934-02-17 The manufacture of aminoalkylated amines Expired GB433625A (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
NL36897D NL36897C (en) 1934-02-17
DER84867D DE602049C (en) 1932-05-10 1932-05-10 Process for introducing aminoalkyl groups into basic groups of organic compounds
GB531134A GB433625A (en) 1934-02-17 1934-02-17 The manufacture of aminoalkylated amines

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB531134A GB433625A (en) 1934-02-17 1934-02-17 The manufacture of aminoalkylated amines

Publications (1)

Publication Number Publication Date
GB433625A true GB433625A (en) 1935-08-19

Family

ID=9793707

Family Applications (1)

Application Number Title Priority Date Filing Date
GB531134A Expired GB433625A (en) 1932-05-10 1934-02-17 The manufacture of aminoalkylated amines

Country Status (2)

Country Link
GB (1) GB433625A (en)
NL (1) NL36897C (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2313352A1 (en) * 1975-06-02 1976-12-31 Texaco Development Corp PROCESS FOR PREPARING NON-CYCLIC POLYALKYLENEPOLYAMINES
FR2313415A1 (en) * 1975-06-02 1976-12-31 Texaco Development Corp PROCESS FOR SELECTIVELY PREPARING ESSENTIALLY NON-CYCLIC POLYALKYLENEPOLYAMINES
FR2313379A1 (en) * 1975-06-02 1976-12-31 Texaco Development Corp PROCESS FOR PREPARING N- (AMINOALKYL) PIPERAZINES

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2313352A1 (en) * 1975-06-02 1976-12-31 Texaco Development Corp PROCESS FOR PREPARING NON-CYCLIC POLYALKYLENEPOLYAMINES
FR2313415A1 (en) * 1975-06-02 1976-12-31 Texaco Development Corp PROCESS FOR SELECTIVELY PREPARING ESSENTIALLY NON-CYCLIC POLYALKYLENEPOLYAMINES
FR2313379A1 (en) * 1975-06-02 1976-12-31 Texaco Development Corp PROCESS FOR PREPARING N- (AMINOALKYL) PIPERAZINES

Also Published As

Publication number Publication date
NL36897C (en)

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