NO117374B - - Google Patents
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- Publication number
- NO117374B NO117374B NO157843A NO15784365A NO117374B NO 117374 B NO117374 B NO 117374B NO 157843 A NO157843 A NO 157843A NO 15784365 A NO15784365 A NO 15784365A NO 117374 B NO117374 B NO 117374B
- Authority
- NO
- Norway
- Prior art keywords
- monocarboxylic acid
- reaction
- group
- alkyl group
- parts
- Prior art date
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- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 239000012948 isocyanate Substances 0.000 claims description 3
- 150000002513 isocyanates Chemical class 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 150000008064 anhydrides Chemical class 0.000 claims description 2
- 150000004982 aromatic amines Chemical class 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000003386 piperidinyl group Chemical group 0.000 claims description 2
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- UFFBMTHBGFGIHF-UHFFFAOYSA-N 2,6-dimethylaniline Chemical compound CC1=CC=CC(C)=C1N UFFBMTHBGFGIHF-UHFFFAOYSA-N 0.000 description 2
- MLPVBIWIRCKMJV-UHFFFAOYSA-N 2-ethylaniline Chemical compound CCC1=CC=CC=C1N MLPVBIWIRCKMJV-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- -1 N-methyl-nipecotic anhydride Chemical compound 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- FBTQQNYGMICJQZ-UHFFFAOYSA-N 1-chloro-2-isocyanato-3-methylbenzene Chemical compound CC1=CC=CC(Cl)=C1N=C=O FBTQQNYGMICJQZ-UHFFFAOYSA-N 0.000 description 1
- AYIXGVABNMIOLK-UHFFFAOYSA-N 1-methylpiperidin-1-ium-3-carboxylate Chemical compound CN1CCCC(C(O)=O)C1 AYIXGVABNMIOLK-UHFFFAOYSA-N 0.000 description 1
- HLNRRPIYRBBHSQ-UHFFFAOYSA-N 1-propylpyrrolidine Chemical compound CCCN1CCCC1 HLNRRPIYRBBHSQ-UHFFFAOYSA-N 0.000 description 1
- CDULGHZNHURECF-UHFFFAOYSA-N 2,3-dimethylaniline 2,4-dimethylaniline 2,5-dimethylaniline 2,6-dimethylaniline 3,4-dimethylaniline 3,5-dimethylaniline Chemical group CC1=CC=C(N)C(C)=C1.CC1=CC=C(C)C(N)=C1.CC1=CC(C)=CC(N)=C1.CC1=CC=C(N)C=C1C.CC1=CC=CC(N)=C1C.CC1=CC=CC(C)=C1N CDULGHZNHURECF-UHFFFAOYSA-N 0.000 description 1
- YQLRKXVEALTVCZ-UHFFFAOYSA-N 2-isocyanato-1,3-dimethylbenzene Chemical compound CC1=CC=CC(C)=C1N=C=O YQLRKXVEALTVCZ-UHFFFAOYSA-N 0.000 description 1
- YCSCBJRBINCWRA-UHFFFAOYSA-N 4-ethoxy-2,6-dimethylaniline Chemical compound CCOC1=CC(C)=C(N)C(C)=C1 YCSCBJRBINCWRA-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- QSACPWSIIRFHHR-UHFFFAOYSA-N dimethylphenyl isocyanide Natural products CC1=CC=CC(C)=C1C#N QSACPWSIIRFHHR-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hcl hcl Chemical compound Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000003589 local anesthetic agent Substances 0.000 description 1
- INWLQCZOYSRPNW-UHFFFAOYSA-N mepivacaine Chemical group CN1CCCCC1C(=O)NC1=C(C)C=CC=C1C INWLQCZOYSRPNW-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
Classifications
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B13/00—Apparatus or processes specially adapted for manufacturing conductors or cables
- H01B13/06—Insulating conductors or cables
- H01B13/14—Insulating conductors or cables by extrusion
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
- B29C48/00—Extrusion moulding, i.e. expressing the moulding material through a die or nozzle which imparts the desired form; Apparatus therefor
- B29C48/15—Extrusion moulding, i.e. expressing the moulding material through a die or nozzle which imparts the desired form; Apparatus therefor incorporating preformed parts or layers, e.g. extrusion moulding around inserts
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
- B29C48/00—Extrusion moulding, i.e. expressing the moulding material through a die or nozzle which imparts the desired form; Apparatus therefor
- B29C48/15—Extrusion moulding, i.e. expressing the moulding material through a die or nozzle which imparts the desired form; Apparatus therefor incorporating preformed parts or layers, e.g. extrusion moulding around inserts
- B29C48/156—Coating two or more articles simultaneously
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B7/00—Insulated conductors or cables characterised by their form
- H01B7/17—Protection against damage caused by external factors, e.g. sheaths or armouring
- H01B7/18—Protection against damage caused by wear, mechanical force or pressure; Sheaths; Armouring
- H01B7/22—Metal wires or tapes, e.g. made of steel
- H01B7/221—Longitudinally placed metal wires or tapes
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B7/00—Insulated conductors or cables characterised by their form
- H01B7/17—Protection against damage caused by external factors, e.g. sheaths or armouring
- H01B7/18—Protection against damage caused by wear, mechanical force or pressure; Sheaths; Armouring
- H01B7/22—Metal wires or tapes, e.g. made of steel
- H01B7/221—Longitudinally placed metal wires or tapes
- H01B7/223—Longitudinally placed metal wires or tapes forming part of a high tensile strength core
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
- B29C48/00—Extrusion moulding, i.e. expressing the moulding material through a die or nozzle which imparts the desired form; Apparatus therefor
- B29C48/03—Extrusion moulding, i.e. expressing the moulding material through a die or nozzle which imparts the desired form; Apparatus therefor characterised by the shape of the extruded material at extrusion
- B29C48/05—Filamentary, e.g. strands
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
- B29C48/00—Extrusion moulding, i.e. expressing the moulding material through a die or nozzle which imparts the desired form; Apparatus therefor
- B29C48/03—Extrusion moulding, i.e. expressing the moulding material through a die or nozzle which imparts the desired form; Apparatus therefor characterised by the shape of the extruded material at extrusion
- B29C48/06—Rod-shaped
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
- B29C48/00—Extrusion moulding, i.e. expressing the moulding material through a die or nozzle which imparts the desired form; Apparatus therefor
- B29C48/03—Extrusion moulding, i.e. expressing the moulding material through a die or nozzle which imparts the desired form; Apparatus therefor characterised by the shape of the extruded material at extrusion
- B29C48/12—Articles with an irregular circumference when viewed in cross-section, e.g. window profiles
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
- Y10T428/2913—Rod, strand, filament or fiber
- Y10T428/2927—Rod, strand, filament or fiber including structurally defined particulate matter
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
- Y10T428/2913—Rod, strand, filament or fiber
- Y10T428/2933—Coated or with bond, impregnation or core
- Y10T428/294—Coated or with bond, impregnation or core including metal or compound thereof [excluding glass, ceramic and asbestos]
- Y10T428/2942—Plural coatings
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
- Y10T428/2913—Rod, strand, filament or fiber
- Y10T428/2933—Coated or with bond, impregnation or core
- Y10T428/294—Coated or with bond, impregnation or core including metal or compound thereof [excluding glass, ceramic and asbestos]
- Y10T428/2958—Metal or metal compound in coating
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
- Y10T428/2913—Rod, strand, filament or fiber
- Y10T428/2933—Coated or with bond, impregnation or core
- Y10T428/294—Coated or with bond, impregnation or core including metal or compound thereof [excluding glass, ceramic and asbestos]
- Y10T428/296—Rubber, cellulosic or silicic material in coating
Description
Fremgangsmåte til fremstilling av N-alkyl- piperidin-monokarbonsyreamid og N-alkyl-pyrrolidin-«-monokarbonsyreamid.
Foreliggende oppfinnelse angår en
fremgangsmåte til fremstilling av N-alkylpiperidin-monokartoonsyreamid og N-alkyl-pyrrolidin-ix-monokarbonsyreamid med de
generelle formler
I disse formler betegner Ri en alkylgruppe, Ri; en lavere alkylgruppe eller et
kloratom, R:1 et hydrogenatom, en hydrok-sylgruppe, en lavere alkylgruppe eller en
alkoksygruppe og Rt betegner et hydrogenatom, et kloratom, en lavere alkylgruppe
eller en alkoksygruppe. Alternativt kan og-så R-, R.i og R-i være hydrogen i samme
forbindelse. Karbonsyreamidgruppen kan
være tilknyttet piperidinringen i alfa-, be-ta- eller gammastillingen.
Nevnte amider har vist seg å være gode
lokalanestetika med liten giftighet i for-hold til sin virkningsgrad.
Ifølge foreliggende oppfinnelse frem-stilles disse forbindelser ved at man lar en
vannfri N-alkylpyridin-monokarbonsyre eller N-alkyl-pyrrolidin-a-monokarbonsyre eller anhydridet, en ester eller kloridet av disse syrer reagere med et aromatisk amin eller et isocyanat som tilsvarer et slikt amin. Fremstillingen utføres ifølge kjente fremgangsmåter.
For terapeutisk bruk er det mest hen-siktsmessig å bruke salter med organiske eller anorganiske syrer av vedkommende amider. Hydrokloridene er funnet å være best egnet.
Fremstillingen av disse forbindelser kan illustreres ved følgende eksempler.
Eksempel 1.
175,5 deler N-etyl-nipecolinsyreklorid-hydroklorid suspenderes i 1700 deler aceton og man lar denne forbindelse reagere med 121 deler 2,6-dimetyl-anilin under avkjøling og kraftig omrøring, idet man sørger for at det opprettholdes en temperatur som ikke overstiger 35° C. Når reaksjonen av-tar etter 1 times etterreaksjon ved 30—35° C, drives acetonet av ved normalt trykk. De siste spor av acetonet fjernes ved hjelp av vakuum. Residuet oppløses i 750 deler vann, oppløsningens pH-verdi innstilles på 5,5, og ikke reagert xylidin ekstraheres med et passende ekstraksjonsmiddel, f. eks. eter, benzol eller toluol. Den vandige oppløsning befries fra rester av ekstraksjonsmidlet ved destillasjon, hvorpå den behandles med 5—10 deler aktivt kull. Etter filtrering utfelles den fri base, N-etylen-nipecotinsyre-
2,6-dimetyianiiid. Basen som utfelles i kry-stallinsk form suges fri for væske, hvorpå den vaskes med vann. I sin alminnelighet er produktet tilstrekkelig rent til å kunne brukes til fremstilling av salter etter at det er tørret i vakuum.
Eksempel 2.
171 deler vannfri N-n-butylpyrrolidin-a-kar,bonsyre oppvarmes sammen med 335 deler 2-klor-6-metyl-fenyl-isocyanat under god omrøring til en temperatur på 90— 110° C. Reaksjonen viser seg ved en sterk utvikling av kulldioksyd, og opphøret av denne kullsyreutvikling viser at reaksjonen er fullført. Overskudd av isocyanat av-destilleres omhyggelig under vakuum. Hele prosessen utføres under god ventilasjon. Til residuet fra reaksjonen tilsettes en ekviva-lent mengde 10—15 pst.'s saltsyre. Opp-løsningen kokes i 15 minutter, avkjøles og uoppløselige reaksjonsprodukter som har dannet seg under reaksjon fjernes ved filtrering. Filtratet inneholder hydrokloridet av N-n-butyl-pyrrolidin-a-monokarbonsyre-2-klor-6-metylanilid som har dannet seg ved reaksjonen. Reaksjonsproduktet vide-rebehandles som angitt i eksempel 1.
Eksempel 3.
167 deler N-n-propyl-pyrrolidin-«-kar-bonsyre oppvarmes langsomt med 121 deler 2- etylanilin, mens det vann som dannes ved reaksjonen drives av ved temperaturer fra 120—230° C. Reaksjonstiden er totalt 6 limer. Residuet fra reaksjonen gjøres surt til en pH-verdi på 3—4 med 10—15 pst.'s saltsyre, og behandlingen fortsettes som angitt i eksempel 1. Reaksjonsproduktet er N-n-propyl-pyrrolidin-a-karbonsyre-2-etylanilid.
Eksempel 4.
268 deler N-metyl-nipecotinsyreanhyd-rid opphetes suksessivt med 165 deler 2,6-dimetyl-4-etoksyanilin til 140—160° C i en total reaksjonstid på 2 timer. Residuet fra reaksjonen gjøres surt til en pH-verdi på 3— 4 med 10—15 pst.'s saltsyre, og behandlingen fortsettes som angitt i eksempel 1. Etter ekstraksjon av det dannede N-metyl-nipecotinsyre-2,6-dimetyl-4-etoksyanilid
gjenvinnes den større del av den N-metyl-nipecotinsyre som også dannes ved reaksjonen som hydroklorid etter inndampning til tørrhet, oppløsning i alkohol, filtrering og inndampning påny.
Eksempel 5. 189,5 deler N-metyl-isonipecotinsyre-etylester oppvarmes sammen med 93 deler anilin ved en temperatur på 180—195° C og den etylalkohol som dannes under reaksjonen drives kontinuerlig av gjennom en kort kolonne. Reaksjonens fullførelse mar-keres ved at avdestillasjonen av etylalkohol opphører. Reaksjonstiden er 8—10 timer. Den videre behandling utføres som angitt i eksempel 1. Reaksjonsproduktet er N-met-yl-isonipecotinsyreanilid.
Eksempel 6. 143 deler absolutt vannfri N-metyl-pipe-colinsyre oppvarmes med 300 deler 2,6-di-metyljfenyl-isocyanat under de i eksempel 2 angitte betingelser. Den videre behandling utføres som angitt i eksempel 1. Reaksjonsproduktet er N-metyl-pipecolinsyre-2,6-dimetylanilid.
Claims (1)
- Fremgangsmåte til fremstilling av N-alkyl-piperidin-monokarbonsyreamid og N-alkyl-pyrrolidin-a-monokarbonsyreamid med de generelle formlerhvor kanbonsyreamidgruppen er tilknyttet piperidinringen i alfa-, beta- eller gammastillingen og i hvilke Ri betegner en alkylgruppe, Ro en lavere alkylgruppe eller et kloratom, Ra et hydrogenatom, en hydrok-sylgruppe, en lavere alkylgruppe eller en alkoksygruppe, Ri betegner et hydrogenatom, et kloratom, en lavere alkylgruppe eller en alkoksygruppe, eller alternativt Rl>, R:i og R4 samtidig betegner hydrogen, karakterisert ved at man bringer en vannfri N-alkylpiperidin-monokarbonsyre eller en N-alkylpyrrolidin-a-monokarbonsyre eller anhydridet, en ester eller kloridet av slike syrer til å reagere med et aromatisk amin eller med et isocyanat som tilsvarer aminet.
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NO157843A NO117374B (no) | 1965-04-27 | 1965-04-27 | |
| GB17688/66A GB1081236A (en) | 1965-04-27 | 1966-04-22 | Method for manufacturing self-supporting cables, including support strands |
| BE680043D BE680043A (no) | 1965-04-27 | 1966-04-26 | |
| DK213966AA DK112961B (da) | 1965-04-27 | 1966-04-27 | Fremgangsmåde til fremstilling af selvbærende kabler med bæreline. |
| AT399266A AT282729B (de) | 1965-04-27 | 1966-04-27 | Selbsttragendes Kabel |
| SE5694/66A SE306827B (no) | 1965-04-27 | 1966-04-27 | |
| ES0326063A ES326063A1 (es) | 1965-04-27 | 1966-04-27 | Metodo para fabricar cables autosoportados con cable soporte. |
| CH610966A CH450510A (de) | 1965-04-27 | 1966-04-27 | Verfahren zur Herstellung eines selbsttragenden Kabels |
| US811274A US3540203A (en) | 1965-04-27 | 1969-03-07 | Self-supporting cables with fine grained powder between support strands and extruded jacket and method of manufacture |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NO157843A NO117374B (no) | 1965-04-27 | 1965-04-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO117374B true NO117374B (no) | 1969-08-04 |
Family
ID=19909169
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO157843A NO117374B (no) | 1965-04-27 | 1965-04-27 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3540203A (no) |
| AT (1) | AT282729B (no) |
| BE (1) | BE680043A (no) |
| CH (1) | CH450510A (no) |
| DK (1) | DK112961B (no) |
| ES (1) | ES326063A1 (no) |
| GB (1) | GB1081236A (no) |
| NO (1) | NO117374B (no) |
| SE (1) | SE306827B (no) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3705489A (en) * | 1970-12-24 | 1972-12-12 | Bethlehem Steel Corp | Wire rope with permanently lubricated core |
| US4017579A (en) * | 1974-11-18 | 1977-04-12 | Consolidated Products Corporation | Method for forming a sheathed electrical cable |
| ATE4734T1 (de) * | 1979-09-18 | 1983-10-15 | Kupferdraht-Isolierwerk Ag Wildegg | Element zur uebertragung von zugkraeften und verwendung desselben als tragorgan fuer freileitungskabel. |
| EP0054784B1 (de) * | 1980-12-19 | 1985-04-10 | Kupferdraht-Isolierwerk AG Wildegg | Freileitungskabel mit Zugentlastungsmitteln |
| EP0133825B1 (fr) * | 1983-06-28 | 1987-09-09 | Elf Atochem S.A. | Matériau composite souple et son procédé de fabrication |
| FR2562467B1 (fr) * | 1984-04-10 | 1986-06-27 | Atochem | Materiau composite souple et son procede de fabrication |
| FR2548084B1 (fr) * | 1983-06-28 | 1985-12-13 | Ato Chimie | Procede de fabrication d'objets composites et objets composites obtenus |
| DE3535267A1 (de) * | 1984-11-17 | 1986-06-05 | Akzo Gmbh, 5600 Wuppertal | Mineralisolierte leitungen |
| US4721587A (en) * | 1985-06-12 | 1988-01-26 | E. I. Du Pont De Nemours And Company | Process of making heat-strengthened yarn |
| JPH064246B2 (ja) * | 1985-12-09 | 1994-01-19 | 富士スタンダ−ドリサ−チ株式会社 | 柔軟性複合材料及びその製造方法 |
| JPS6340764A (ja) * | 1986-08-02 | 1988-02-22 | 株式会社アクロス | 無機質繊維強化炭素複合材料用の柔軟性中間材及びその製造方法 |
| JPH0737435A (ja) * | 1993-07-26 | 1995-02-07 | Mitsubishi Electric Corp | 絶縁電線 |
| US5678609A (en) * | 1995-03-06 | 1997-10-21 | Arnco Corporation | Aerial duct with ribbed liner |
| JP5892072B2 (ja) * | 2013-01-08 | 2016-03-23 | 日立金属株式会社 | 車両用複合ケーブル |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2386634A (en) * | 1940-03-20 | 1945-10-09 | Sprague Electric Co | Flexible electrical insulating layer |
| US2567162A (en) * | 1948-01-14 | 1951-09-04 | Du Pont | Coated electrical conductor and method of making same |
| US3197593A (en) * | 1960-04-25 | 1965-07-27 | Nat Ind As | Electrical current-limiting fuse |
| DE1106381B (de) * | 1960-06-08 | 1961-05-10 | Chem Fab Dr Franz & Rutenbeck | Selbsttragende isolierte elektrische Leitung oder selbsttragendes Kabel |
| US3267201A (en) * | 1963-10-04 | 1966-08-16 | Superior Cable Corp | Bonded messenger cable with messenger adhesively bonded to a common support jacket |
-
1965
- 1965-04-27 NO NO157843A patent/NO117374B/no unknown
-
1966
- 1966-04-22 GB GB17688/66A patent/GB1081236A/en not_active Expired
- 1966-04-26 BE BE680043D patent/BE680043A/xx unknown
- 1966-04-27 CH CH610966A patent/CH450510A/de unknown
- 1966-04-27 AT AT399266A patent/AT282729B/de not_active IP Right Cessation
- 1966-04-27 ES ES0326063A patent/ES326063A1/es not_active Expired
- 1966-04-27 SE SE5694/66A patent/SE306827B/xx unknown
- 1966-04-27 DK DK213966AA patent/DK112961B/da unknown
-
1969
- 1969-03-07 US US811274A patent/US3540203A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| SE306827B (no) | 1968-12-09 |
| ES326063A1 (es) | 1967-03-01 |
| DK112961B (da) | 1969-02-03 |
| CH450510A (de) | 1968-01-31 |
| GB1081236A (en) | 1967-08-31 |
| US3540203A (en) | 1970-11-17 |
| AT282729B (de) | 1970-07-10 |
| BE680043A (no) | 1966-10-26 |
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