GB518989A - Manufacture of acylamino-morpholine compounds - Google Patents
Manufacture of acylamino-morpholine compoundsInfo
- 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
Links
- 238000004519 manufacturing process Methods 0.000 title 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 6
- 239000002253 acid Substances 0.000 abstract 4
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 abstract 4
- -1 ethylene, phenylene Chemical group 0.000 abstract 4
- 239000000203 mixture Substances 0.000 abstract 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 3
- 150000007513 acids Chemical class 0.000 abstract 3
- 125000003277 amino group Chemical group 0.000 abstract 3
- 238000006243 chemical reaction Methods 0.000 abstract 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 abstract 2
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 abstract 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 abstract 2
- 229960003750 ethyl chloride Drugs 0.000 abstract 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 abstract 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 abstract 2
- 229940050176 methyl chloride Drugs 0.000 abstract 2
- 150000002780 morpholines Chemical class 0.000 abstract 2
- CSFAYIHXWKUTHH-UHFFFAOYSA-N n-phenylmorpholin-4-amine Chemical compound C1COCCN1NC1=CC=CC=C1 CSFAYIHXWKUTHH-UHFFFAOYSA-N 0.000 abstract 2
- WTBAHSZERDXKKZ-UHFFFAOYSA-N octadecanoyl chloride Chemical compound CCCCCCCCCCCCCCCCCC(Cl)=O WTBAHSZERDXKKZ-UHFFFAOYSA-N 0.000 abstract 2
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 abstract 2
- 229940067157 phenylhydrazine Drugs 0.000 abstract 2
- 150000003142 primary aromatic amines Chemical class 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 abstract 2
- QLAJNZSPVITUCQ-UHFFFAOYSA-N 1,3,2-dioxathietane 2,2-dioxide Chemical compound O=S1(=O)OCO1 QLAJNZSPVITUCQ-UHFFFAOYSA-N 0.000 abstract 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 abstract 1
- HDMDXJAWWCMBSV-UHFFFAOYSA-N 4-(3-methylphenyl)morpholine Chemical compound CC1=CC=CC(N2CCOCC2)=C1 HDMDXJAWWCMBSV-UHFFFAOYSA-N 0.000 abstract 1
- OLAFVASCPJETBP-UHFFFAOYSA-N 4-(4-methylphenyl)morpholine Chemical compound C1=CC(C)=CC=C1N1CCOCC1 OLAFVASCPJETBP-UHFFFAOYSA-N 0.000 abstract 1
- PGWMWXXBOYUUAW-UHFFFAOYSA-N 4-[(4-morpholin-4-ylphenyl)methylamino]benzenesulfonic acid Chemical compound N1(CCOCC1)C1=CC=C(CNC2=CC=C(S(=O)(=O)O)C=C2)C=C1 PGWMWXXBOYUUAW-UHFFFAOYSA-N 0.000 abstract 1
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 abstract 1
- 239000005639 Lauric acid Substances 0.000 abstract 1
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical class C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 abstract 1
- PXHPPJJETFHTOK-UHFFFAOYSA-O N-[2-methyl-4-(4-methylmorpholin-4-ium-4-yl)phenyl]octadecanamide Chemical compound CC=1C=C(C=CC1NC(CCCCCCCCCCCCCCCCC)=O)[N+]1(CCOCC1)C PXHPPJJETFHTOK-UHFFFAOYSA-O 0.000 abstract 1
- ZKXDGKXYMTYWTB-UHFFFAOYSA-N N-nitrosomorpholine Chemical compound O=NN1CCOCC1 ZKXDGKXYMTYWTB-UHFFFAOYSA-N 0.000 abstract 1
- BXWUYZBFLVOIOI-UHFFFAOYSA-N NC1=CC=CC=C1.ClNC1=CC=CC=C1 Chemical compound NC1=CC=CC=C1.ClNC1=CC=CC=C1 BXWUYZBFLVOIOI-UHFFFAOYSA-N 0.000 abstract 1
- PRCGISKSQQCZTB-UHFFFAOYSA-N S(=O)(C1=CC=C(C=C1)N)(=O)O.C1(=CC=CC=C1)N1CCOCC1 Chemical compound S(=O)(C1=CC=C(C=C1)N)(=O)O.C1(=CC=CC=C1)N1CCOCC1 PRCGISKSQQCZTB-UHFFFAOYSA-N 0.000 abstract 1
- 230000001476 alcoholic effect Effects 0.000 abstract 1
- 239000002168 alkylating agent Substances 0.000 abstract 1
- 230000002152 alkylating effect Effects 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- WGQKYBSKWIADBV-UHFFFAOYSA-N aminomethyl benzene Natural products NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 150000008064 anhydrides Chemical class 0.000 abstract 1
- 239000012435 aralkylating agent Substances 0.000 abstract 1
- 125000000732 arylene group Chemical group 0.000 abstract 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 abstract 1
- 229940073608 benzyl chloride Drugs 0.000 abstract 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 abstract 1
- 235000019864 coconut oil Nutrition 0.000 abstract 1
- 239000003240 coconut oil Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 230000008878 coupling Effects 0.000 abstract 1
- 238000010168 coupling process Methods 0.000 abstract 1
- 238000005859 coupling reaction Methods 0.000 abstract 1
- 150000004985 diamines Chemical class 0.000 abstract 1
- 150000008049 diazo compounds Chemical class 0.000 abstract 1
- 235000014113 dietary fatty acids Nutrition 0.000 abstract 1
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 abstract 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- NQGIJDNPUZEBRU-UHFFFAOYSA-N dodecanoyl chloride Chemical compound CCCCCCCCCCCC(Cl)=O NQGIJDNPUZEBRU-UHFFFAOYSA-N 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 229930195729 fatty acid Natural products 0.000 abstract 1
- 239000000194 fatty acid Substances 0.000 abstract 1
- 150000004665 fatty acids Chemical class 0.000 abstract 1
- 230000004151 fermentation Effects 0.000 abstract 1
- 238000000855 fermentation Methods 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 230000004048 modification Effects 0.000 abstract 1
- 238000012986 modification Methods 0.000 abstract 1
- MKQLBNJQQZRQJU-UHFFFAOYSA-N morpholin-4-amine Chemical compound NN1CCOCC1 MKQLBNJQQZRQJU-UHFFFAOYSA-N 0.000 abstract 1
- 230000000802 nitrating effect Effects 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 229950000244 sulfanilic acid Drugs 0.000 abstract 1
- 150000004992 toluidines Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic 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
- C07D295/02—Heterocyclic 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
- C07D295/037—Heterocyclic 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic 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
- C07D295/04—Heterocyclic 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
- C07D295/12—Heterocyclic 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
- C07D295/135—Heterocyclic 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic 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
- C07D295/22—Heterocyclic 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
- C07D295/28—Nitrogen atoms
- C07D295/32—Nitrogen 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.
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)
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 |
-
1938
- 1938-09-14 GB GB26800/38A patent/GB518989A/en not_active Expired
Cited By (1)
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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