BE516958A - - Google Patents
Info
- Publication number
- BE516958A BE516958A BE516958DA BE516958A BE 516958 A BE516958 A BE 516958A BE 516958D A BE516958D A BE 516958DA BE 516958 A BE516958 A BE 516958A
- Authority
- BE
- Belgium
- Prior art keywords
- boiling
- under
- methyl
- carboline
- radical
- Prior art date
Links
- 238000000034 method Methods 0.000 claims description 10
- -1 N-substituted phenylhydrazines Chemical class 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 238000009835 boiling Methods 0.000 description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 239000000155 melt Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- SXUYRJBNPFPWTA-UHFFFAOYSA-N 1-methylpiperidin-1-ium-4-one;chloride Chemical compound Cl.CN1CCC(=O)CC1 SXUYRJBNPFPWTA-UHFFFAOYSA-N 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- WOLUYEFMPZAHNN-UHFFFAOYSA-N 1-(2-bromoethoxy)butane Chemical compound CCCCOCCBr WOLUYEFMPZAHNN-UHFFFAOYSA-N 0.000 description 1
- IONWMQBHSDINJP-UHFFFAOYSA-N 1-(2-ethoxyethyl)-1-phenylhydrazine Chemical compound CCOCCN(N)C1=CC=CC=C1 IONWMQBHSDINJP-UHFFFAOYSA-N 0.000 description 1
- CJTNLEQLKKYLFO-UHFFFAOYSA-N 1-butoxyethanol Chemical group CCCCOC(C)O CJTNLEQLKKYLFO-UHFFFAOYSA-N 0.000 description 1
- GGYVTHJIUNGKFZ-UHFFFAOYSA-N 1-methylpiperidin-2-one Chemical compound CN1CCCCC1=O GGYVTHJIUNGKFZ-UHFFFAOYSA-N 0.000 description 1
- OTNNTCJQDSEITO-UHFFFAOYSA-N 1-methylpiperidin-2-one;hydrochloride Chemical compound Cl.CN1CCCCC1=O OTNNTCJQDSEITO-UHFFFAOYSA-N 0.000 description 1
- BAPOBTZBOWUIHB-UHFFFAOYSA-N 2-(2-chloroethylsulfanyl)propane Chemical compound CC(C)SCCCl BAPOBTZBOWUIHB-UHFFFAOYSA-N 0.000 description 1
- NAMYKGVDVNBCFQ-UHFFFAOYSA-N 2-bromopropane Chemical compound CC(C)Br NAMYKGVDVNBCFQ-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 208000001431 Psychomotor Agitation Diseases 0.000 description 1
- 206010038743 Restlessness Diseases 0.000 description 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 125000004103 aminoalkyl group Chemical group 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 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
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- SAXLSLVMGUSPIY-UHFFFAOYSA-N n-(2-butoxyethyl)aniline Chemical compound CCCCOCCNC1=CC=CC=C1 SAXLSLVMGUSPIY-UHFFFAOYSA-N 0.000 description 1
- LJPICRWPKJNFFL-UHFFFAOYSA-N n-(2-propan-2-yloxyethyl)aniline Chemical compound CC(C)OCCNC1=CC=CC=C1 LJPICRWPKJNFFL-UHFFFAOYSA-N 0.000 description 1
- 230000009935 nitrosation Effects 0.000 description 1
- 238000007034 nitrosation reaction Methods 0.000 description 1
- 229940075930 picrate Drugs 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Hydrogenated Pyridines (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE516958A true BE516958A (enrdf_load_stackoverflow) |
Family
ID=153994
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE516958D BE516958A (enrdf_load_stackoverflow) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE516958A (enrdf_load_stackoverflow) |
-
0
- BE BE516958D patent/BE516958A/fr unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH375017A (fr) | Procédé de préparation de nouveaux dérivés de l'imidazole | |
| CH407088A (fr) | Procédé de préparation de dérivés des acides 4-halo-3-sulfamoyl-benzoïques | |
| EP0376850A1 (fr) | Dérivés du benzène, leur préparation et compositions pharmaceutiques les contenant | |
| WO1990003972A1 (fr) | Derives de methyl-4 ((phenyl-4 piperazinyl-1)-2 ethyl)-5 thiazole | |
| BE516958A (enrdf_load_stackoverflow) | ||
| FR2503705A1 (fr) | Derives de phenethanolamine, leur preparation et leur application en therapeutique | |
| EP0002401B1 (fr) | Dérivés de naphtalène, leur préparation et leur application en thérapeutique | |
| CH640818A5 (fr) | Derives d'acide naphtyl-1 acetique, leurs procedes de preparation et medicament les contenant. | |
| CH623818A5 (en) | Process for producing derivatives of thiochroman | |
| BE884977A (fr) | Nouveau n-phenyl-benzamides utiles dans le traitement de l'inflammation et de la douleur des mammiferes | |
| BE879730R (fr) | Derives d'alkylenediamines | |
| BE541651A (enrdf_load_stackoverflow) | ||
| CH495951A (fr) | Procédé de préparation de nouvelles bases azotées contenant un radical naphtyle ou naphtyl-méthyle | |
| BE495129A (enrdf_load_stackoverflow) | ||
| CH371117A (fr) | Procédé de préparation de trichlorométhyl-oxazolid-4-ones | |
| BE572291A (enrdf_load_stackoverflow) | ||
| BE633474A (enrdf_load_stackoverflow) | ||
| BE572277A (enrdf_load_stackoverflow) | ||
| CH365381A (fr) | Procédé pour la préparation de dérivés de la pipérazine | |
| BE532238A (enrdf_load_stackoverflow) | ||
| FR2594122A1 (fr) | ((pyrrolidinyl-1)-2 ethyoxy)-3 p cymene, les derives acetyl, acetoxy, hydroxy dudit produit et les medicaments contenant lesdits composes comme principe actif | |
| CH396031A (fr) | Procédé de préparation de nouveaux dérivés hydraziniques | |
| BE542106A (enrdf_load_stackoverflow) | ||
| FR2624857A1 (fr) | Derives de nicotinoyl-piperazine, procede de preparation et utilisation en therapeutique | |
| BE417585A (enrdf_load_stackoverflow) |