Showing content from https://patents.google.com/patent/GB765544A/en below:
GB765544A - Production of amides and ketones having basic substituents
GB765544A - Production of amides and ketones having basic substituents - Google PatentsProduction of amides and ketones having basic substituents Info
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Publication number
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GB765544A
GB765544A GB6298/55A GB629855A GB765544A GB 765544 A GB765544 A GB 765544A GB 6298/55 A GB6298/55 A GB 6298/55A GB 629855 A GB629855 A GB 629855A GB 765544 A GB765544 A GB 765544A
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Authority
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GB
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United Kingdom
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Prior art keywords
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ketone
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alkyl
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xylidide
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starting materials
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amine
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Prior art date
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1954-03-03
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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.)
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Expired
Application number
GB6298/55A
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.)
FRIEDERIKE FEDORA AUSLANDER
HILLEL REMEDY FACTORY Ltd
Original Assignee
FRIEDERIKE FEDORA AUSLANDER
HILLEL REMEDY FACTORY Ltd
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.)
1954-03-03
Filing date
1955-03-03
Publication date
1957-01-09
1955-03-03 Application filed by FRIEDERIKE FEDORA AUSLANDER, HILLEL REMEDY FACTORY Ltd filed Critical FRIEDERIKE FEDORA AUSLANDER
1957-01-09 Publication of GB765544A publication Critical patent/GB765544A/en
Status Expired legal-status Critical Current
Links
- 150000001408 amides Chemical class 0.000 title abstract 4
- 150000002576 ketones Chemical class 0.000 title abstract 4
- -1 polymethylene Polymers 0.000 abstract 5
- 239000007858 starting material Substances 0.000 abstract 4
- 239000002253 acid Substances 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 abstract 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 abstract 2
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 abstract 2
- 239000000370 acceptor Substances 0.000 abstract 2
- 229910052783 alkali metal Inorganic materials 0.000 abstract 2
- 150000001412 amines Chemical class 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- ZTHRQJQJODGZHV-UHFFFAOYSA-N n-phenylpropanamide Chemical compound CCC(=O)NC1=CC=CC=C1 ZTHRQJQJODGZHV-UHFFFAOYSA-N 0.000 abstract 2
- 150000003335 secondary amines Chemical class 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- YXWWHNCQZBVZPV-UHFFFAOYSA-N 2'-methylacetophenone Chemical compound CC(=O)C1=CC=CC=C1C YXWWHNCQZBVZPV-UHFFFAOYSA-N 0.000 abstract 1
- 101100496169 Arabidopsis thaliana CLH1 gene Proteins 0.000 abstract 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 1
- 101100044057 Mesocricetus auratus SYCP3 gene Proteins 0.000 abstract 1
- 101100080600 Schizosaccharomyces pombe (strain 972 / ATCC 24843) nse6 gene Proteins 0.000 abstract 1
- 229960001413 acetanilide Drugs 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000001769 aryl amino group Chemical group 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 101150111293 cor-1 gene Proteins 0.000 abstract 1
- 150000004292 cyclic ethers Chemical class 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 150000001983 dialkylethers Chemical class 0.000 abstract 1
- 239000012458 free base Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- FFHGCIYKPNISDY-UHFFFAOYSA-N n-(4-chlorophenyl)propanamide Chemical compound CCC(=O)NC1=CC=C(Cl)C=C1 FFHGCIYKPNISDY-UHFFFAOYSA-N 0.000 abstract 1
- POOMBLVZFRPIBC-UHFFFAOYSA-N n-(chloromethyl)ethanamine Chemical compound CCNCCl POOMBLVZFRPIBC-UHFFFAOYSA-N 0.000 abstract 1
- FDBSRZMPVJHVAC-UHFFFAOYSA-N n-chloro-n-cyclohexylcyclohexanamine Chemical compound C1CCCCC1N(Cl)C1CCCCC1 FDBSRZMPVJHVAC-UHFFFAOYSA-N 0.000 abstract 1
- TYDFLVGVWMSQAC-UHFFFAOYSA-N n-chloro-n-ethylethanamine Chemical compound CCN(Cl)CC TYDFLVGVWMSQAC-UHFFFAOYSA-N 0.000 abstract 1
- MAGVJLLHDZWQFM-UHFFFAOYSA-N n-chloro-n-methylmethanamine Chemical compound CN(C)Cl MAGVJLLHDZWQFM-UHFFFAOYSA-N 0.000 abstract 1
- ZLARYUDVCNJSFV-UHFFFAOYSA-N n-chloro-n-propylpropan-1-amine Chemical compound CCCN(Cl)CCC ZLARYUDVCNJSFV-UHFFFAOYSA-N 0.000 abstract 1
- FSSVIYSWRLKICW-UHFFFAOYSA-N n-ethyl-n-phenylacetamide Chemical compound CCN(C(C)=O)C1=CC=CC=C1 FSSVIYSWRLKICW-UHFFFAOYSA-N 0.000 abstract 1
- LMTGCJANOQOGPI-UHFFFAOYSA-N n-methyl-n-phenylacetamide Chemical compound CC(=O)N(C)C1=CC=CC=C1 LMTGCJANOQOGPI-UHFFFAOYSA-N 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- KRIOVPPHQSLHCZ-UHFFFAOYSA-N propiophenone Chemical compound CCC(=O)C1=CC=CC=C1 KRIOVPPHQSLHCZ-UHFFFAOYSA-N 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 150000003512 tertiary amines Chemical class 0.000 abstract 1
Classifications
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- 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
- C07D295/10—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 doubly bound oxygen or sulphur atoms
- C07D295/104—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 doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/108—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 doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The hydrohalide of an amide or ketone having the general formula: <FORM:0765544/IV(b)/1> wherein R is a hydrogen atom or an alkyl, aryl or aralkyl group, R1 is an aryl group or an aryl-amino group which may contain alkyl groups or halogen atoms as nuclear substituents and/or an alkyl substituent on the nitrogen atom of the amino group, R2 and R3 are both alkyl or cycloalkyl groups or together represent a polymethylene or alkyl-substituted polymethylene group, and Hal is a halogen atom, is prepared by treating an amide or ketone R.CH2.COR1 with an N-halogeno secondary amine R2.N(Hal).R3 in an inert solvent. Suitable solvents are dialkyl ethers, cyclic ethers or carbon tetrahalides. If an acid acceptor is present in the reaction the product is a free base. Acid acceptors referred to are an excess of the secondary amine, a tertiary amine and an alkali metal salt of a weak acid. Amine starting materials referred to are N-chlordimethylamine, N - chlormethylethylamine, N - chlordiethylamine, N - chlordi - n - propylamine, N - chlordi - p - butylamine, N - chloropiperidine and N-chlorodicyclohexylamine. Ketone starting materials include acetophenone, propiophenone, methyl tolyl ketone, ethyl tolyl ketone and methyl xylyl ketone, and amide starting materials include acetanilide, aceto-ortho-toluidine, acet - para - toluidide, acet - 2.4 - xylidide, acet-2,6 - xylidide, propionanilide propion - 2.4-xylidide, propion - 2.6 - xylidide, orthochloroacetanilide, para - chloroacetanilide, 2.4-, 2.5 - dichloroacetanilide and 2.4, 6 - trichloroacetanilides, para - chloropropionanilide, N - methylacetanilide and N - ethylacetanilide. Examples describe the preparation of 2.6-dimethyl - N.N. - diethyl glycylanilide, 2.5 - di - chloro - N.N. - di - n - propyl alanylanilide, a -piperidinopropiophenone hydrochloride and a -dimethylaminodesoxybenzoin. Starting materials. N-Halogeno secondary amines are prepared from the appropriate secondary amine and a cold aqueous solution of an alkali metal hypohalite, preferably in the presence of a solvent for the amine.
GB6298/55A 1954-03-03 1955-03-03 Production of amides and ketones having basic substituents Expired GB765544A (en) Applications Claiming Priority (1) Application Number Priority Date Filing Date Title IL765544X 1954-03-03 Publications (1) Publication Number Publication Date GB765544A true GB765544A (en) 1957-01-09 Family ID=11056276 Family Applications (1) Application Number Title Priority Date Filing Date GB6298/55A Expired GB765544A (en) 1954-03-03 1955-03-03 Production of amides and ketones having basic substituents Country Status (1) Cited By (3) * Cited by examiner, â Cited by third party Publication number Priority date Publication date Assignee Title US3287217A (en) * 1966-11-22 Compositions and methods for stimulat- ing the central nervous system and in- creasing the blood pressure US3305562A (en) * 1960-05-24 1967-02-21 Wander Ag Dr A Process for making alpha-pyrrolidino-valerophenones US3314970A (en) * 1967-04-18 Pykrolidino ketones
Cited By (3) * Cited by examiner, â Cited by third party Publication number Priority date Publication date Assignee Title US3287217A (en) * 1966-11-22 Compositions and methods for stimulat- ing the central nervous system and in- creasing the blood pressure US3314970A (en) * 1967-04-18 Pykrolidino ketones US3305562A (en) * 1960-05-24 1967-02-21 Wander Ag Dr A Process for making alpha-pyrrolidino-valerophenones Similar Documents Publication Publication Date Title GB1138405A (en) 1969-01-01 Morpholine derivatives GB765544A (en) 1957-01-09 Production of amides and ketones having basic substituents GB1024816A (en) 1966-04-06 Basic ethers of substituted hydroxy benzoic acids and process for making same GB1080807A (en) 1967-08-23 Heterocyclic amino-isobutyl compounds GB924608A (en) 1963-04-24 Improvements in or relating to 1.2.4-oxadiazoles and processes for producing the same GB959203A (en) 1964-05-27 Indole derivatives and salts thereof ES297620A1 (en) 1964-07-01 Procedure for obtaining derivatives of phenoxyactic acid (Machine-translation by Google Translate, not legally binding) ES406098A1 (en) 1976-03-01 Substituted 2,6-dinitroanilines and herbicidal compositions containing them US2623045A (en) 1952-12-23 N-(substituted-aminoethyl) 4-aminobenzoic acid diethylaminoethyl esters GB842322A (en) 1960-07-27 Aminoguanidine derivatives GB1109308A (en) 1968-04-10 Heterocyclic alkanoic acid amides GB871235A (en) 1961-06-21 Novel substituted pyrrolidones and salts thereof and a process for the manufacture of same GB881359A (en) 1961-11-01 New quaternary ammonium salts, their production and pharmaceutical compositions containing them ES287547A1 (en) 1963-06-16 Procedure for the production of N- (2,3-dimethylene) antranilic acid and its salts (Machine-translation by Google Translate, not legally binding) GB880334A (en) 1961-10-18 New hydrazinium compounds, their production and pharmaceutical compositions containing them GB920755A (en) 1963-03-13 Basically substituted phenyl-thiocarbamic acid-s-esters GB771875A (en) 1957-04-03 Process for the production of monoquaternary ammonium compounds GB898068A (en) 1962-06-06 Amino compounds GB864146A (en) 1961-03-29 Aralkylaminoalkyl hydrazines GB904680A (en) 1962-08-29 Process for the production of o-quinones GB847205A (en) 1960-09-07 A process for the manufacture of ethylenimine derivatives and novel ethylenimine derivatives GB952592A (en) 1964-03-18 Derivatives of 4:4-bis(4-hydroxyphenyl)-pentanoic acid and methods of preparing the same GB615006A (en) 1948-12-31 Improvements in the manufacture of heterocyclic compounds ES228914A3 (en) 1956-09-01 A procedure for the preparation of non-substitute aminoalquilbenzhydrylic etheries and nioethics (Machine-translation by Google Translate, not legally binding) GB859445A (en) 1961-01-25 Basically substituted alkyl xanthine derivatives and acid addition salts thereof and a process for their production
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