NO117868B - - Google Patents
Download PDFInfo
- Publication number
- NO117868B NO117868B NO15715365A NO15715365A NO117868B NO 117868 B NO117868 B NO 117868B NO 15715365 A NO15715365 A NO 15715365A NO 15715365 A NO15715365 A NO 15715365A NO 117868 B NO117868 B NO 117868B
- Authority
- NO
- Norway
- Prior art keywords
- parts
- acid
- solution
- dissolved
- alkyl group
- Prior art date
Links
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 150000001408 amides Chemical class 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 150000004982 aromatic amines Chemical class 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 150000004820 halides Chemical class 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000003386 piperidinyl group Chemical group 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 239000000243 solution Substances 0.000 description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 10
- 239000003513 alkali Substances 0.000 description 9
- 239000003610 charcoal Substances 0.000 description 8
- 238000010992 reflux Methods 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- -1 piperidine monocarboxylic acid halide Chemical class 0.000 description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hcl hcl Chemical compound Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 3
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 150000003839 salts Chemical class 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
- HXEACLLIILLPRG-YFKPBYRVSA-N L-pipecolic acid Chemical compound [O-]C(=O)[C@@H]1CCCC[NH2+]1 HXEACLLIILLPRG-YFKPBYRVSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- HXEACLLIILLPRG-RXMQYKEDSA-N l-pipecolic acid Natural products OC(=O)[C@H]1CCCCN1 HXEACLLIILLPRG-RXMQYKEDSA-N 0.000 description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- ZGONCYGWELXUPA-AWEZNQCLSA-N (2S)-1-butyl-N-(2-chloro-6-methylphenyl)pyrrolidine-2-carboxamide Chemical compound ClC1=C(NC([C@H]2N(CCC2)CCCC)=O)C(=CC=C1)C ZGONCYGWELXUPA-AWEZNQCLSA-N 0.000 description 1
- VTVJMWZZVJSEMO-BYPYZUCNSA-N (2s)-pyrrolidine-2-carbonyl chloride Chemical compound ClC(=O)[C@@H]1CCCN1 VTVJMWZZVJSEMO-BYPYZUCNSA-N 0.000 description 1
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 1
- NAMYKGVDVNBCFQ-UHFFFAOYSA-N 2-bromopropane Chemical compound CC(C)Br NAMYKGVDVNBCFQ-UHFFFAOYSA-N 0.000 description 1
- WFNLHDJJZSJARK-UHFFFAOYSA-N 2-chloro-6-methylaniline Chemical compound CC1=CC=CC(Cl)=C1N WFNLHDJJZSJARK-UHFFFAOYSA-N 0.000 description 1
- KIHUWAOTZVYMFH-UHFFFAOYSA-N 4-butoxy-2,6-dimethylaniline Chemical compound CCCCOC1=CC(C)=C(N)C(C)=C1 KIHUWAOTZVYMFH-UHFFFAOYSA-N 0.000 description 1
- ZXPJSNYLHALLGL-UHFFFAOYSA-N CC(C=CC=C1C)=C1NC(C(CCCC1)N1C1CCCC1)=O Chemical compound CC(C=CC=C1C)=C1NC(C(CCCC1)N1C1CCCC1)=O ZXPJSNYLHALLGL-UHFFFAOYSA-N 0.000 description 1
- DSYFCRKFHZVMOS-UHFFFAOYSA-N CCCCOC(C=C1C)=CC(C)=C1NC(C1N(C)CCCC1)=O Chemical compound CCCCOC(C=C1C)=CC(C)=C1NC(C1N(C)CCCC1)=O DSYFCRKFHZVMOS-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- VUHKTERBGMWQAY-UHFFFAOYSA-N N-(2-ethylphenyl)-1-propan-2-ylpiperidine-3-carboxamide Chemical compound C(C)C1=C(NC(C2CN(CCC2)C(C)C)=O)C=CC=C1 VUHKTERBGMWQAY-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 150000003931 anilides Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- AQNQQHJNRPDOQV-UHFFFAOYSA-N bromocyclohexane Chemical compound BrC1CCCCC1 AQNQQHJNRPDOQV-UHFFFAOYSA-N 0.000 description 1
- BRTFVKHPEHKBQF-UHFFFAOYSA-N bromocyclopentane Chemical compound BrC1CCCC1 BRTFVKHPEHKBQF-UHFFFAOYSA-N 0.000 description 1
- 229940008406 diethyl sulfate Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- SRJOCJYGOFTFLH-UHFFFAOYSA-N isonipecotic acid Chemical compound OC(=O)C1CCNCC1 SRJOCJYGOFTFLH-UHFFFAOYSA-N 0.000 description 1
- 239000003589 local anesthetic agent Substances 0.000 description 1
- 229960005015 local anesthetics Drugs 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- INWLQCZOYSRPNW-UHFFFAOYSA-N mepivacaine Chemical compound CN1CCCCC1C(=O)NC1=C(C)C=CC=C1C INWLQCZOYSRPNW-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 1
- AALBZAYEBOEAPQ-UHFFFAOYSA-N n-(2,6-dimethylphenyl)-1-ethylpiperidine-2-carboxamide Chemical compound CCN1CCCCC1C(=O)NC1=C(C)C=CC=C1C AALBZAYEBOEAPQ-UHFFFAOYSA-N 0.000 description 1
- DNZSDACGXYHMOL-UHFFFAOYSA-N n-(2-ethylphenyl)piperidine-3-carboxamide Chemical compound CCC1=CC=CC=C1NC(=O)C1CNCCC1 DNZSDACGXYHMOL-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000725 suspension 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
Classifications
-
- H—ELECTRICITY
- H04—ELECTRIC COMMUNICATION TECHNIQUE
- H04J—MULTIPLEX COMMUNICATION
- H04J3/00—Time-division multiplex systems
- H04J3/17—Time-division multiplex systems in which the transmission channel allotted to a first user may be taken away and re-allotted to a second user if the first user becomes inactive, e.g. TASI
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT654664 | 1964-03-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO117868B true NO117868B (de) | 1969-10-06 |
Family
ID=11121186
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO15715365A NO117868B (de) | 1964-03-24 | 1965-03-10 |
Country Status (8)
| Country | Link |
|---|---|
| AT (1) | AT265376B (de) |
| BE (1) | BE661547A (de) |
| CH (1) | CH427922A (de) |
| DE (1) | DE1267288B (de) |
| FR (1) | FR1438322A (de) |
| GB (1) | GB1078483A (de) |
| NL (1) | NL148211B (de) |
| NO (1) | NO117868B (de) |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE604025C (de) * | 1931-11-14 | 1934-10-13 | Standard Elek Zitaets Ges A G | Schaltungsanordnung fuer Fernmelde-, insbesondere Fernsprechanlagen mit Gegenverkehr |
| DE1072656B (de) * | 1957-09-26 | 1960-01-07 | Western Electric Company Incorporated New York, N Y (V St A) | , und Carl Brandt Henry Feldman Belleair Clearwater, Fla (V St A) I Zeitteilungs-Multiplex-Fernsprechsystem |
-
1965
- 1965-02-19 CH CH236165A patent/CH427922A/it unknown
- 1965-03-02 NL NL6502645A patent/NL148211B/xx unknown
- 1965-03-03 FR FR7757A patent/FR1438322A/fr not_active Expired
- 1965-03-10 NO NO15715365A patent/NO117868B/no unknown
- 1965-03-18 AT AT246665A patent/AT265376B/de active
- 1965-03-19 DE DE19651267288 patent/DE1267288B/de not_active Withdrawn
- 1965-03-23 GB GB1217865A patent/GB1078483A/en not_active Expired
- 1965-03-24 BE BE661547D patent/BE661547A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NL148211B (nl) | 1975-12-15 |
| NL6502645A (de) | 1965-09-27 |
| GB1078483A (en) | 1967-08-09 |
| DE1267288B (de) | 1968-05-02 |
| FR1438322A (fr) | 1966-05-13 |
| CH427922A (it) | 1967-01-15 |
| AT265376B (de) | 1968-10-10 |
| BE661547A (de) | 1965-07-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US3419560A (en) | 1-aminoalkyl 2-aryl indanes and tetrahydronaphthalenes | |
| NO123148B (de) | ||
| US2792399A (en) | Anilides of heterocyclic compounds | |
| NO117374B (de) | ||
| PL184767B1 (pl) | Sposób wytwarzania monohydratu chlorowodorku ropiwakainy | |
| NO117868B (de) | ||
| US2838509A (en) | 9-aminoalkyl-9-xanthenecarboxamides | |
| US2933530A (en) | Method of producing quaternary ammonium compounds | |
| US2800474A (en) | 9-(piperazinoalkyl) norharman derivatives | |
| NO139920B (no) | Fremgangsmaate ved fremstilling av 2,5-disubstituerte benzamider | |
| US3103515A (en) | Basic esters of i-benzoxacycloalkane- | |
| SU609464A3 (ru) | Способ получени производных -/2-пирролидинилметил/ бензамидов или их солей | |
| US2880209A (en) | Piperazine quaternary salts having parasitical activity and method of making | |
| JP2009535327A (ja) | ロピバカイン塩酸塩無水物およびその調製 | |
| NO143084B (no) | Innretning for skallfjerning av marine krepsdyr, spesielt antarktisk krill. | |
| US2734920A (en) | New chemical compounds and their | |
| DE69737529T2 (de) | Herstellung von 1-butyl-4-piperidinylmethylamin | |
| NO135092B (de) | ||
| US3378592A (en) | Process for the production of 3, 4-dihydroxybenzyloxyaminehydrobromide | |
| SU434654A3 (ru) | Способ получения производных тропан-3-ола | |
| US2535971A (en) | 1-carbalkoxy-4-substituted piperazines | |
| US2980683A (en) | Process for preparing beta-substitutedethyl piperazines | |
| SU449485A3 (ru) | Способ получени -замещенных сложных эфиров 1,2,3,6-тетрагидро-4пиридилметилкарбоновой кислоты | |
| US3128276A (en) | Optionally alpha-substituted 1-amino-2,3, or 4-(cyclohexyl/- phenyl) methylpiperidines and precursors | |
| US3198835A (en) | Pyrenyl methyl tertiary amino amines |