GB940035A - New tri- and tetra-substituted alkylenediamines and acid addition salts thereof - Google Patents

New tri- and tetra-substituted alkylenediamines and acid addition salts thereof

Info

Publication number
GB940035A
GB940035A GB43202/60A GB4320260A GB940035A GB 940035 A GB940035 A GB 940035A GB 43202/60 A GB43202/60 A GB 43202/60A GB 4320260 A GB4320260 A GB 4320260A GB 940035 A GB940035 A GB 940035A
Authority
GB
United Kingdom
Prior art keywords
phenethyl
aniline
prepared
general formula
compound
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
GB43202/60A
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.)
Novartis AG
National Starch and Chemical Investment Holding Corp
Original Assignee
JR Geigy AG
National Starch and Chemical Investment Holding Corp
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 JR Geigy AG, National Starch and Chemical Investment Holding Corp filed Critical JR Geigy AG
Publication of GB940035A publication Critical patent/GB940035A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
    • C07C211/26—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring
    • C07C211/27—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring having amino groups linked to the six-membered aromatic ring by saturated carbon chains
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton

Abstract

The invention comprises tri- and tetrasubstituted alkylenediamines of the general formula <FORM:0940035/C2/1> (wherein R1 represents a hydrogen atom or an alkyl radical having 1-6 carbon atoms, R2 and R3 represent alkyl radicals of at most 6 carbon atoms or, together with the nitrogen atom to which they are bound, form a pyrrolidino, piperidino or morpholino radical, and Z represents an alkylene radical containing at most 6 carbon atoms in a straight or branched chain) and acid addition salts thereof, and their preparation by condensing 2- (b -phenethyl)- aniline or an N-C1-6 alkyl-2-(b -phenethyl)-aniline with a reactive ester of HO-Z-NR2R3, optionally followed by salt formation. The substituted alkylenediames, which have anti-allergic, anti-convulsive, serotonin-antagonistic and anaesthesia-potentiating activity, may also be prepared by (a) condensing a reactive ester of a compound of the general formula <FORM:0940035/C2/2> with HNR2R3, (b) reducing a compound of the general formula <FORM:0940035/C2/3> (wherein R11, R21, R31 and Z1 each correspond to R1, R2, R3 and Z, respectively, except that in at least one of them at least one methylene group bound to a nitrogen atom is replaced by a carbonyl group), (c) reducing a compound of the general formula <FORM:0940035/C2/4> or (d)-when R1 represents a C1-6 alkyl radical-alkylating the corresponding compound in which R1 is a hydrogen atom. N-Methyl-2-(b -phenethyl)-aniline is prepared by methylating N-p-tolylsulphonyl-2- (b -phenethyl)-aniline and hydrolysing the resulting N-methyl-N-p-tolysulphonyl-2-(b -phenethyl)-aniline. N-Ethyl-2-(b -phenethyl)-aniline is prepared similarly. N-n-Propyl-2-(b -phenethyl)-aniline is prepared by (a) treating 2-(b -phenethyl)-aniline with n-propyl bromide in the presence of sodamide, and (b) refluxing a mixture of 2-(b -phenethyl)-aniline, propionaldehyde and ethanol, dissolving the product in a large quantity of ethanol and subjecting it to catalytic hydrogenation. N-n-Butyl-2-(b -phenethyl)-aniline is prepared by treating 2-(b -phenethyl)-aniline with n-butyl bromide in the presence of sodamide.
GB43202/60A 1959-12-16 1960-12-15 New tri- and tetra-substituted alkylenediamines and acid addition salts thereof Expired GB940035A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH8187259A CH386443A (en) 1959-12-16 1959-12-16 Process for the preparation of new tetrasubstituted alkylenediamines

Publications (1)

Publication Number Publication Date
GB940035A true GB940035A (en) 1963-10-23

Family

ID=4539193

Family Applications (1)

Application Number Title Priority Date Filing Date
GB43202/60A Expired GB940035A (en) 1959-12-16 1960-12-15 New tri- and tetra-substituted alkylenediamines and acid addition salts thereof

Country Status (2)

Country Link
CH (1) CH386443A (en)
GB (1) GB940035A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3974158A (en) * 1972-08-11 1976-08-10 Imperial Chemical Industries Limited 2-(Substituted anilino)methylmorpholines

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SE388603B (en) * 1971-01-15 1976-10-11 Merck & Co Inc PROCEDURE FOR THE PREPARATION OF A PHENYL ALKYLAR ALKYLAMINE WITH ANTIARTHMIC EFFECT

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3974158A (en) * 1972-08-11 1976-08-10 Imperial Chemical Industries Limited 2-(Substituted anilino)methylmorpholines
US3974156A (en) * 1972-08-11 1976-08-10 Imperial Chemical Industries Limited 2-(Substituted anilino) methylmorpholine compounds

Also Published As

Publication number Publication date
CH386443A (en) 1965-01-15

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