GB518989A - Manufacture of acylamino-morpholine compounds - Google Patents

Manufacture of acylamino-morpholine compounds

Info

Publication number
GB518989A
GB518989A GB26800/38A GB2680038A GB518989A GB 518989 A GB518989 A GB 518989A GB 26800/38 A GB26800/38 A GB 26800/38A GB 2680038 A GB2680038 A GB 2680038A GB 518989 A GB518989 A GB 518989A
Authority
GB
United Kingdom
Prior art keywords
chloride
morpholine
acid
condensing
formaldehyde
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
GB26800/38A
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
Original Assignee
JR Geigy 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
Application filed by JR Geigy AG filed Critical JR Geigy AG
Publication of GB518989A publication Critical patent/GB518989A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D295/00Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/02Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
    • C07D295/037Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements with quaternary ring nitrogen atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D295/00Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/12Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
    • C07D295/135Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D295/00Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/22Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
    • C07D295/28Nitrogen atoms
    • C07D295/32Nitrogen atoms acylated with carboxylic or carbonic acids, or their nitrogen or sulfur analogues

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Abstract

518,989. Acylamino-morpholine compounds. GEIGY AKT.-GES., J. R. Sept. 14, 1938, No. 26800. Convention date, June 11. [Class 2 (iii)] Acylamino-morpholine compounds of high surface activity are prepared by reacting a morpholine derivative containing attached to the nuclear nitrogen atom, either directly or through an alkylene, arylene, or aralkylene group, an amino-group having at least one reactive hydrogen atom, with a carboxylic acid containing at least 6 carbon atoms or a mixture of such acids or with the anhydride or a halide or ester of such an acid or mixture of acids. In a modification, a product obtained by the reaction of an aryl-morpholine with formaldehyde and a primary aromatic amine which is not capable of forming a.stable anhydro-compound with formaldehyde, or a sulphonic acid of such an amine, is acylated by reaction with an amide of a carboxylic acid containing at least 6 carbon atoms or of a mixture of such acids. The intermediate morpholine derivatives can be prepared by converting nitroso-morpholine to N-aminomorpholine or by condensing a hydrazine having a non-substituted amino-group, e.g., phenylhydrazine with #: #<1>-dichloroethyl ether to produce phenylaminomorpholine; or by condensing a diamine, e.g., ethylene, phenylene or naphthylene diamine with #:#<1>-dichloroethyl ether ; or by condensing a monoaminoarylcompound, e.g., aniline chloraniline, nitraniline or toluidine, with #:#<1>-dichloroethyl ether and introducing a nuclear amino-group, e.g., by nitrating or nitrosating or coupling with a diazo-compound and subsequently reducing or reductively cleaving ; or by reacting the arylmorpholine with formaldehyde and a primary aromatic amine or amino-aromatic sulphonic acid, which forms no stable anhydro-compound with formaldehyde, e.g., para-toluidine or sulphanilic acid, to produce a substituted paramorphinyl - benzyl - amine. The acylaminomorpholine compounds react with known alkylating or aralkylating agents, e.g., methyl, ethyl or benzyl chloride, methyl ethyl or allyl bromide, or dimethyl sulphate to form morpholinium salts. In examples : (1) N-meta-tolylmorpholine is nitrosated and reduced and the product is heated on the water-bath with stearic acid chloride ; the acylamino compound is treated with dimethyl sulphate or allyl bromide to form (3-methyl-4-stearoylamino-phenyl)- methylmorpholinium methosulphate or the corresponding allyl-morpholinium bromide ; (ii) N-para-tolylmorpholine is nitrated, reduced and then treated with the chloride of the mixture of the fatty acids from coconut oil ; the morpholium salt is prepared using methyl chloride ; (iii) meta-aminophenyl-morpholine (prepared by condensing #:#<1>-dichlorethyl ether and meta-nitraniline and reducing) is reacted with the chloride of commercial lauric acid and then heated with dimethyl or diethyl sulphate ; (iv) the product of reaction of #:#<1>-dichlorethyl ether and para-phenylenediamine is reacted with the chloride of fermentation caproic acid and converted into the quaternary salt by means of ethyl chloride ; (v) an aqueous alcoholic solution of phenyl-morpholine sulphanilate is mixed with formaldehyde to produce N-(4- morpholinyl-benzyl)-sulphanilic acid which is heated with stearic acid chloride and ammonia in an autoclave for hours, and the product is treated with dimethyl sulphate ; (vi) phenylaminomorpholine (prepared by condensing phenylhydrazine and #:#<1>-dichlorethyl ether) is acylated with lauric acid chloride, and the product is heated with dimethyl sulphate.
GB26800/38A 1938-06-11 1938-09-14 Manufacture of acylamino-morpholine compounds Expired GB518989A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH518989X 1938-06-11

Publications (1)

Publication Number Publication Date
GB518989A true GB518989A (en) 1940-03-13

Family

ID=4517846

Family Applications (1)

Application Number Title Priority Date Filing Date
GB26800/38A Expired GB518989A (en) 1938-06-11 1938-09-14 Manufacture of acylamino-morpholine compounds

Country Status (1)

Country Link
GB (1) GB518989A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2562384A (en) * 1949-10-05 1951-07-31 John J Mccabe Jr Preparation of quaternary ammonium salts of acylated aminoethyl morpholines

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2562384A (en) * 1949-10-05 1951-07-31 John J Mccabe Jr Preparation of quaternary ammonium salts of acylated aminoethyl morpholines

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