BE519855A - - Google Patents
Info
- Publication number
- BE519855A BE519855A BE519855DA BE519855A BE 519855 A BE519855 A BE 519855A BE 519855D A BE519855D A BE 519855DA BE 519855 A BE519855 A BE 519855A
- Authority
- BE
- Belgium
- Prior art keywords
- iodide
- piperazine
- general formula
- methyl
- cyclohexyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 9
- 150000003839 salts Chemical group 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 5
- 150000001450 anions Chemical class 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 150000004885 piperazines Chemical class 0.000 claims description 4
- 231100000331 toxic Toxicity 0.000 claims description 3
- 230000002588 toxic effect Effects 0.000 claims description 3
- YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical compound [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical class C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 9
- 239000002585 base Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 7
- 239000000155 melt Substances 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 5
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
- 238000005956 quaternization reaction Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- -1 1,1-Diethyl-4-benzhydryl-piperazinium bromide Chemical compound 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- HVWJHIOFMOFXAE-UHFFFAOYSA-N 1-benzhydryl-2,5-dimethylpiperazine Chemical compound CC1CNC(C)CN1C(C=1C=CC=CC=1)C1=CC=CC=C1 HVWJHIOFMOFXAE-UHFFFAOYSA-N 0.000 description 2
- NSMWYRLQHIXVAP-UHFFFAOYSA-N 2,5-dimethylpiperazine Chemical compound CC1CNC(C)CN1 NSMWYRLQHIXVAP-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- MSQACBWWAIBWIC-UHFFFAOYSA-N hydron;piperazine;chloride Chemical compound Cl.C1CNCCN1 MSQACBWWAIBWIC-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- MCEUCOMSCDMLPY-UHFFFAOYSA-N piperazin-1-ium;iodide Chemical compound I.C1CNCCN1 MCEUCOMSCDMLPY-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 229940066771 systemic antihistamines piperazine derivative Drugs 0.000 description 2
- OQUSCPYIGRKEOO-UHFFFAOYSA-N 1-(2,2-diphenylethyl)piperazine Chemical compound C1CNCCN1CC(C=1C=CC=CC=1)C1=CC=CC=C1 OQUSCPYIGRKEOO-UHFFFAOYSA-N 0.000 description 1
- GGDQXHMKZFVUIB-UHFFFAOYSA-N 1-benzhydryl-2,4,5-trimethylpiperazine Chemical compound CC1CN(C)C(C)CN1C(C=1C=CC=CC=1)C1=CC=CC=C1 GGDQXHMKZFVUIB-UHFFFAOYSA-N 0.000 description 1
- RNKRCXJQXZKCSY-UHFFFAOYSA-N 2-benzhydryl-1-methylpiperazine Chemical compound CN1CCNCC1C(C=1C=CC=CC=1)C1=CC=CC=C1 RNKRCXJQXZKCSY-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- VDDNOZATPNYRFL-UHFFFAOYSA-M 4-benzhydryl-1,1-diethyl-2,5-dimethylpiperazin-1-ium;iodide Chemical group [I-].C1C(C)[N+](CC)(CC)CC(C)N1C(C=1C=CC=CC=1)C1=CC=CC=C1 VDDNOZATPNYRFL-UHFFFAOYSA-M 0.000 description 1
- HHRLVDFSVUQPMS-UHFFFAOYSA-M 4-benzhydryl-1-methyl-1-propan-2-ylpiperazin-1-ium;iodide Chemical compound [I-].C1C[N+](C(C)C)(C)CCN1C(C=1C=CC=CC=1)C1=CC=CC=C1 HHRLVDFSVUQPMS-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 238000006957 Michael reaction Methods 0.000 description 1
- 229910021607 Silver chloride Inorganic materials 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- ZDVDCDLBOLSVGM-UHFFFAOYSA-N [chloro(phenyl)methyl]benzene Chemical compound C=1C=CC=CC=1C(Cl)C1=CC=CC=C1 ZDVDCDLBOLSVGM-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- NWVNXDKZIQLBNM-UHFFFAOYSA-N diphenylmethylpiperazine Chemical compound C1CNCCN1C(C=1C=CC=CC=1)C1=CC=CC=C1 NWVNXDKZIQLBNM-UHFFFAOYSA-N 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 1
- LJQKCYFTNDAAPC-UHFFFAOYSA-N ethanol;ethyl acetate Chemical compound CCO.CCOC(C)=O LJQKCYFTNDAAPC-UHFFFAOYSA-N 0.000 description 1
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 150000004694 iodide salts Chemical group 0.000 description 1
- 229940049920 malate Drugs 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 229940102396 methyl bromide Drugs 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- WKDROHPCPSLGLA-UHFFFAOYSA-N piperazin-1-ium;sulfate Chemical compound [O-]S([O-])(=O)=O.C1C[NH2+]CCN1.C1C[NH2+]CCN1 WKDROHPCPSLGLA-UHFFFAOYSA-N 0.000 description 1
- UXWKNNJFYZFNDI-UHFFFAOYSA-N piperazine;dihydrobromide Chemical compound Br.Br.C1CNCCN1 UXWKNNJFYZFNDI-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 1
- 230000002048 spasmolytic effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- 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
- C07D295/02—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 containing only hydrogen and carbon atoms in addition to the ring hetero elements
- C07D295/037—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 containing only hydrogen and carbon atoms in addition to the ring hetero elements with quaternary ring nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE519855A true BE519855A (d) |
Family
ID=155938
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE519855D BE519855A (d) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE519855A (d) |
-
0
- BE BE519855D patent/BE519855A/fr unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| FR2656610A1 (fr) | Derives d'amino-2 phenyl-4 thiazole, leur procede de preparation et leur application therapeutique. | |
| EP0612716B1 (fr) | Procédé pour la préparation d'un aminoalcool optiquement pur | |
| BE519855A (d) | ||
| FR2669030A1 (fr) | Nouveaux derives d'imidazole, leur procede de preparation et les compositions pharmaceutiques qui les contiennent. | |
| CA1253153A (fr) | Derives d'(arylpiperazinylethylaminoethoxy)-4 phenol, leur methode de preparation et leur application therapeutique | |
| CA1183849A (fr) | ¬alkyl- et alcenyl-3 piperidyl-4)-2 ethyl|-3 indoles et leur utilisation comme medicaments | |
| BE739678A (fr) | Amino-alcools et leur preparation | |
| FR2494696A1 (fr) | Nouveau procede de preparation de steroides 3-amines et leurs sels | |
| FR2473512A1 (fr) | Nouveaux 2-aminomethyl-6-halogeno-phenols, leur preparation et leur application comme medicaments | |
| BE485826A (d) | ||
| BE664212A (d) | ||
| CH284618A (fr) | Procédé de préparation de la N-méthyl-N'-(4-chlorobenzhydryl)-pipérazine. | |
| BE558994A (d) | ||
| BE517656A (d) | ||
| BE551306A (d) | ||
| BE504403A (d) | ||
| CH586185A5 (en) | Alpha-amino-alcohols prepn. - by reacting epoxides with allylic alcohols, tosylating, and reacting with ammonia | |
| BE508515A (d) | ||
| BE535650A (d) | ||
| CH354081A (fr) | Procédé de préparation de nouveaux esters de l'acide phénothiazinyl-10-carboxylique | |
| CH365381A (fr) | Procédé pour la préparation de dérivés de la pipérazine | |
| BE569837A (d) | ||
| BE721233A (d) | ||
| BE508095A (d) | ||
| BE531936A (d) |