GB547301A - Improvements in and relating to the synthesis of aromatic and heterocyclic n-(amino-alkyl) substituted amines - Google Patents

Improvements in and relating to the synthesis of aromatic and heterocyclic n-(amino-alkyl) substituted amines

Info

Publication number
GB547301A
GB547301A GB756341A GB756341A GB547301A GB 547301 A GB547301 A GB 547301A GB 756341 A GB756341 A GB 756341A GB 756341 A GB756341 A GB 756341A GB 547301 A GB547301 A GB 547301A
Authority
GB
United Kingdom
Prior art keywords
diethylamino
compounds
methylbutyl
alkyl
hydrochloride
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
GB756341A
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
Priority to GB756341A priority Critical patent/GB547301A/en
Publication of GB547301A publication Critical patent/GB547301A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
    • C07D219/04—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems 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 carbon atoms of the ring system
    • C07D219/08—Nitrogen atoms
    • C07D219/10—Nitrogen atoms attached in position 9
    • C07D219/12—Amino-alkylamino radicals attached in position 9

Landscapes

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

Abstract

547,301. Aminoalkylamino compounds. BERGMAN, E. Nov. 14, 1940, No. 7563/41. [Class 2 (iii)] Compounds of the formula Ar. NH. CHR 3 . R. N.<<SP>R1</SP> R2 in which R represents an aryl group or a benzopyridine residue, R stands for an aliphatic hydrocarbon chain, R 1 and R 2 signify hydrogen or alkyl groups which latter may form part of an alkylene ring, and R 3 represents hydrogen or alkyl, are prepared by reducing compounds Ar.NH 2 under substantially neutral conditions in the presence of an amino-aldehyde OCH. R. N <<SP>R1</SP> R2 or anamino-ketone R 3 . CO. R. N<<SP>R1</SP> R2 The reduction is preferably carried out with hydrogen in the presence of such catalysts as palladium, platinum and nickel. Examples describe the preparation of (1) #-diethylaminoethyl-p-anisidine by the hydrogenation of p-anisidine and diethyl-aminoacetaldehyde hydrochloride in the presence of Raney nickel; (2) #-diethylamino-α-methylbutyl-aniline by hydrogenating aniline and 5-diethylaminopentanone-2 in the presence of Raney nickel and trimethylamine hydrochloride; (3) (8- diethylamino-α-methylbutyl)-2-chloraniline by reducing a mixture of 2-chloraniline and 5- diethylamino-pentanone-2 with zinc and an acid ; (4) #-diethylamino-α-methylbutyl-1- naphthylamine by the hydrogenation of 1- naphthylamine and 5-diethylamino-pentanone- 2 in the presence of palladium-barium sulphate and diethylamine hydrochloride. A list of other products is given, including #-diethylaminoethyl-9-aminoacridine, 8-(#-diethylaminoethylamino)-quinoline, and compounds containing chloro and carboxyl groups.
GB756341A 1940-11-14 1940-11-14 Improvements in and relating to the synthesis of aromatic and heterocyclic n-(amino-alkyl) substituted amines Expired GB547301A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB756341A GB547301A (en) 1940-11-14 1940-11-14 Improvements in and relating to the synthesis of aromatic and heterocyclic n-(amino-alkyl) substituted amines

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB756341A GB547301A (en) 1940-11-14 1940-11-14 Improvements in and relating to the synthesis of aromatic and heterocyclic n-(amino-alkyl) substituted amines

Publications (1)

Publication Number Publication Date
GB547301A true GB547301A (en) 1942-08-21

Family

ID=9835516

Family Applications (1)

Application Number Title Priority Date Filing Date
GB756341A Expired GB547301A (en) 1940-11-14 1940-11-14 Improvements in and relating to the synthesis of aromatic and heterocyclic n-(amino-alkyl) substituted amines

Country Status (1)

Country Link
GB (1) GB547301A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3291808A (en) * 1961-08-14 1966-12-13 Parke Davis & Co Naphthalene diamine compounds and methods for their production
US4922021A (en) * 1981-03-04 1990-05-01 Basf Aktiensellschaft New alkylene diamine derivatives

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3291808A (en) * 1961-08-14 1966-12-13 Parke Davis & Co Naphthalene diamine compounds and methods for their production
US4922021A (en) * 1981-03-04 1990-05-01 Basf Aktiensellschaft New alkylene diamine derivatives

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