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GB726545A - Process for the preparation of secondary benzyl arylamines and benzyl heterocyclic amines - Google Patents

Process for the preparation of secondary benzyl arylamines and benzyl heterocyclic amines

Info

Publication number
GB726545A
GB726545A GB2380/53A GB238053A GB726545A GB 726545 A GB726545 A GB 726545A GB 2380/53 A GB2380/53 A GB 2380/53A GB 238053 A GB238053 A GB 238053A GB 726545 A GB726545 A GB 726545A
Authority
GB
United Kingdom
Prior art keywords
benzylamino
benzyl
dibenzylamino
naphthalene
benzyl alcohol
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
GB2380/53A
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.)
Individual
Original Assignee
Individual
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 Individual filed Critical Individual
Publication of GB726545A publication Critical patent/GB726545A/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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pyridine Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

Secondary benzyl-arylamines and benzylamino-heterocyclic compounds of aromatic character are obtained by reacting the corresponding primary amines with benzyl alcohol in the presence of anhydrous alkali hydroxide, the water formed by the reaction being continually removed from the reaction mixture, e.g. by distillation; the arylamine or heterocyclic amine and/or the benzyl alcohol may contain alkyl, aryl, alkoxy, aryloxy, alkylamino or arylamino nuclear substituents. The benzyl alcohol is preferably used in slight excess of the theoretical amount. The reaction is facilitated by the presence of a small amount of the corresponding aldehyde. Examples show the production of the following: N-benzyl - aniline, m - benzylamino - toluene, p-benzylamino - diphenylamine, 2 - benzylamino - naphthalene, 2 : 6 - dibenzylaminopyridine, m - dibenzylamino - benzene, 2-benzylamino - diphenyl, 4 - benzylaminodiphenyl, 4 : 41 - dibenzylamino - diphenylether, 1 : 5 - dibenzylamino - naphthalene and 2 - benzylamino - 4 - methylpyridine. Other products obtainable by this process are o-benzylamino - toluene, p - benzylaminoanisole, 1 - benzylamino - naphthalene, p-dibenzylamino - benzene, 2 - benzylaminopyridine and N-(p-methoxybenzyl)-aniline.
GB2380/53A 1952-02-07 1953-01-27 Process for the preparation of secondary benzyl arylamines and benzyl heterocyclic amines Expired GB726545A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
IL726545X 1952-02-07

Publications (1)

Publication Number Publication Date
GB726545A true GB726545A (en) 1955-03-23

Family

ID=11055259

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2380/53A Expired GB726545A (en) 1952-02-07 1953-01-27 Process for the preparation of secondary benzyl arylamines and benzyl heterocyclic amines

Country Status (1)

Country Link
GB (1) GB726545A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3019262A (en) * 1956-01-09 1962-01-30 Firestone Tire & Rubber Co Nu-benzyl-n'-phenyl-p-phenylenediamine and its manufacture
CN103288722A (en) * 2013-05-08 2013-09-11 温州大学 High-selectivity synthesis method of secondary amine

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3019262A (en) * 1956-01-09 1962-01-30 Firestone Tire & Rubber Co Nu-benzyl-n'-phenyl-p-phenylenediamine and its manufacture
CN103288722A (en) * 2013-05-08 2013-09-11 温州大学 High-selectivity synthesis method of secondary amine

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