NO121522B - - Google Patents
Download PDFInfo
- Publication number
- NO121522B NO121522B NO156184A NO15618464A NO121522B NO 121522 B NO121522 B NO 121522B NO 156184 A NO156184 A NO 156184A NO 15618464 A NO15618464 A NO 15618464A NO 121522 B NO121522 B NO 121522B
- Authority
- NO
- Norway
- Prior art keywords
- ethyl
- benzhydryl
- piperidine
- solution
- acid
- Prior art date
Links
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 8
- JDPAFKBSDMDTLY-UHFFFAOYSA-N 2-benzhydryl-1-ethylpiperidine Chemical compound C(C)N1C(CCCC1)C(C1=CC=CC=C1)C1=CC=CC=C1 JDPAFKBSDMDTLY-UHFFFAOYSA-N 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 5
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 4
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 4
- 235000019253 formic acid Nutrition 0.000 claims description 4
- LLOQMFDCQPKSFB-UHFFFAOYSA-N 1-benzhydrylpiperidine Chemical class C1CCCCN1C(C=1C=CC=CC=1)C1=CC=CC=C1 LLOQMFDCQPKSFB-UHFFFAOYSA-N 0.000 claims description 3
- -1 hydrogen halogen Chemical class 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 230000021962 pH elevation Effects 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
- 239000000243 solution Substances 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 4
- VRZVPALEJCLXPR-UHFFFAOYSA-N ethyl 4-methylbenzenesulfonate Chemical compound CCOS(=O)(=O)C1=CC=C(C)C=C1 VRZVPALEJCLXPR-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- FQYYIPZPELSLDK-UHFFFAOYSA-N ethyl pyridine-2-carboxylate Chemical compound CCOC(=O)C1=CC=CC=N1 FQYYIPZPELSLDK-UHFFFAOYSA-N 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 3
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 3
- 229910003446 platinum oxide Inorganic materials 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- LOCZWXXWEGXCLL-UHFFFAOYSA-N ethyl 1-ethylpiperidine-2-carboxylate Chemical compound CCOC(=O)C1CCCCN1CC LOCZWXXWEGXCLL-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- QILSFLSDHQAZET-UHFFFAOYSA-N diphenylmethanol Chemical compound C=1C=CC=CC=1C(O)C1=CC=CC=C1 QILSFLSDHQAZET-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000021 stimulant Substances 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/42—Introducing metal atoms or metal-containing groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/55—Boron-containing compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEV0025293 | 1964-01-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO121522B true NO121522B (de) | 1971-03-08 |
Family
ID=7581816
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO156184A NO121522B (de) | 1964-01-31 | 1964-12-29 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3347819A (de) |
| AT (1) | AT257156B (de) |
| BE (1) | BE656196A (de) |
| CH (1) | CH450726A (de) |
| DE (1) | DE1545158A1 (de) |
| ES (1) | ES307734A1 (de) |
| GB (1) | GB1023931A (de) |
| NL (1) | NL6501049A (de) |
| NO (1) | NO121522B (de) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3907746A (en) * | 1972-02-23 | 1975-09-23 | Ici Inc | Stabilized polyamides |
| JPS5177690A (en) * | 1974-12-27 | 1976-07-06 | Sekisui Chemical Co Ltd | Ensoganjujushino netsuanteikashorihoho |
| DE3201780A1 (de) * | 1982-01-21 | 1983-08-25 | Henkel KGaA, 4000 Düsseldorf | Neue polymere organo-borverbindungen und ihre verwendung |
| DE4030399A1 (de) * | 1990-09-26 | 1992-04-02 | Basf Ag | Makromolekuele des propylens mit einem funktionellen kettenende |
-
1964
- 1964-01-31 DE DE19641545158 patent/DE1545158A1/de active Pending
- 1964-11-23 CH CH1508464A patent/CH450726A/de unknown
- 1964-11-25 BE BE656196D patent/BE656196A/xx unknown
- 1964-12-29 NO NO156184A patent/NO121522B/no unknown
- 1964-12-31 ES ES0307734A patent/ES307734A1/es not_active Expired
-
1965
- 1965-01-25 GB GB3187/65A patent/GB1023931A/en not_active Expired
- 1965-01-26 US US428240A patent/US3347819A/en not_active Expired - Lifetime
- 1965-01-26 AT AT66165A patent/AT257156B/de active
- 1965-01-28 NL NL6501049A patent/NL6501049A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB1023931A (en) | 1966-03-30 |
| BE656196A (de) | 1965-03-16 |
| AT257156B (de) | 1967-09-25 |
| ES307734A1 (es) | 1965-04-16 |
| NL6501049A (de) | 1965-08-02 |
| DE1545158A1 (de) | 1970-01-22 |
| US3347819A (en) | 1967-10-17 |
| CH450726A (de) | 1968-01-31 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH618170A5 (de) | ||
| NO118710B (de) | ||
| US3119826A (en) | Piperazine derivatives | |
| NO119899B (de) | ||
| NO162176B (no) | Middel for bekjempelse av plantesykdommer og anvendelse derav. | |
| NO139918B (no) | Nye ioniske jodbenzenderivater for anvendelse i roentgenkontrastmidler | |
| NO163552B (no) | Sammensatt understell. | |
| NO121522B (de) | ||
| NO127606B (de) | ||
| NO762505L (de) | ||
| US3171858A (en) | alpha-ethylamino-o-methylisobutyrophenone | |
| SU564805A3 (ru) | Способ получени производных -(3,3-дифенилпропил)пропилендиамина или их солей | |
| NO121340B (de) | ||
| GOTO et al. | (+)-Codeine and (+)-morphine from sinomenine | |
| US3943173A (en) | 3-Alkylamino- alpha-aminomethyl-4-hydroxybenzyl alcohols | |
| US2883394A (en) | New indole derivatives | |
| NO743281L (de) | ||
| Marion et al. | The Synthesis of l-Roemerine1 | |
| SU393268A1 (ru) | Способ получения 2-метил-6-аминогептанола-2 | |
| US2719847A (en) | Substituted l-benzyl-z-methyl-octahy- | |
| US3786154A (en) | Compositions and method employing 1-(4-hydroxy-3'-(hydroxymethyl)-phenyl)1-hydroxy-2-aralkylaminoethanes | |
| Atkinson et al. | 733. Triazaphenanthrenes. Part II. Derivatives of 10-phenyl-1: 2: 9-triazaphenanthrene | |
| US3251832A (en) | Desoxo^schizozygins and process for producing the same | |
| AT324314B (de) | Verfahren zur herstellung von neuen 4-(m-benzoylphenyl)-butan (bzw. -buten-2)-sauren | |
| SU126116A1 (ru) | Способ получени 5-окситриптофана |