BE773937A - Procede de preparation d'aroyl-alkyl-piperidines - Google Patents
Procede de preparation d'aroyl-alkyl-piperidinesInfo
- Publication number
- BE773937A BE773937A BE773937A BE773937A BE773937A BE 773937 A BE773937 A BE 773937A BE 773937 A BE773937 A BE 773937A BE 773937 A BE773937 A BE 773937A BE 773937 A BE773937 A BE 773937A
- Authority
- BE
- Belgium
- Prior art keywords
- emi
- omega
- aroyl
- alkylpiperidines
- decarboxylation
- Prior art date
Links
- 238000006114 decarboxylation reaction Methods 0.000 title 1
- 238000000034 method Methods 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 239000005457 ice water Substances 0.000 claims 1
- 239000002244 precipitate Substances 0.000 claims 1
- 238000010992 reflux Methods 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 abstract description 2
- 238000006243 chemical reaction Methods 0.000 abstract description 2
- 229940125723 sedative agent Drugs 0.000 abstract description 2
- 239000000932 sedative agent Substances 0.000 abstract description 2
- 239000003513 alkali Substances 0.000 abstract 1
- 210000003169 central nervous system Anatomy 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 230000006103 sulfonylation Effects 0.000 description 1
- 238000005694 sulfonylation reaction Methods 0.000 description 1
- -1 sulfonyloxy group Chemical group 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/52—Oxygen atoms attached in position 4 having an aryl radical as the second substituent in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/10—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
- C07D211/14—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/70—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Hydrogenated Pyridines (AREA)
Description
La présente invention concerne un procéda <EMI ID=1.1> ridines de la formule : <EMI ID=2.1> <EMI ID=3.1> un radical oxhydryle et n est -on nombre entier valant <EMI ID=4.1> <EMI ID=5.1> <EMI ID=6.1> pas satisfaisants, car ils nécessitent des opérations <EMI ID=7.1> <EMI ID=8.1> <EMI ID=9.1> <EMI ID=10.1> <EMI ID=11.1> <EMI ID=12.1> <EMI ID=13.1> dical alkyle inférieur, tel que méthyle, éthyle, propy- <EMI ID=14.1> un reste d'acide actif, tel qu'un atome d'halogène (de chlore ou de brome) ou un groupe sulfonyloxy aromatique <EMI ID=15.1> Le schéma 1 ci-dessus concerne la - préparation <EMI ID=16.1> <EMI ID=17.1> Dans le premier stade, on fait réagir un compo- <EMI ID=18.1> inerte, tel que le benzène, le toluène, le xylène, l'éther, <EMI ID=19.1> <EMI ID=20.1> <EMI ID=21.1> <EMI ID=22.1> Le schéma II concerne la préparation d'un compose III. <EMI ID=23.1> <EMI ID=24.1> <EMI ID=25.1> Le premier stade en consiste en une réaction . <EMI ID=26.1> <EMI ID=27.1> composé VIII, c'est-à-dire le formaldéhyde, peut être employé sous forme d'une solution aqueuse, mais 1* emploi du paraformaldéhyde est cependant préféré. La transformation du composé X en composé XI est obtenue dans un second stade par un traitement du pre- <EMI ID=28.1> tique de sulfonylation, tel que le chlorure de p-toluènesulfcnyle, dans un solvant inerte tel que le benzène, - le <EMI ID=29.1> <EMI ID=30.1> un traitement du composé XI dans un solvant inerte, tel que l'anhydride acétique, l'acide acétique ou le chloroforme, <EMI ID=31.1> chlorure d'hydrogène, suivi d'un traitement du produit obtenu par l'eau. <EMI ID=32.1> la formule I sont connus et sont des sédatifs utiles pour <EMI ID=33.1> sont des composés .nouveaux, qui possèdent égalisent une <EMI ID=34.1> l'hydroxyde de sodium aqueux et on extrait au toluène* La <EMI ID=35.1> <EMI ID=36.1> <EMI ID=37.1> <EMI ID=38.1> A la-température ordinaire, on ajoute du.carbonate de po- <EMI ID=39.1> solution au toluène* La couche organique est séchée sur sulfate de magnésium et évaporée sous pression réduite. <EMI ID=40.1>
Claims (1)
- <EMI ID=41.1>est évaporée sous pression réduite et on retient unehuile jaune.<EMI ID=42.1><EMI ID=43.1>chauffe pendant 30 minutes à reflux. Le précipité., qui<EMI ID=44.1>est versé dans de J'eau glacée, ce qui provoque une pré-<EMI ID=45.1><EMI ID=46.1><EMI ID=47.1>substitué ou non, R désigne un atome d'hydrogène ou un <EMI ID=48.1> <EMI ID=49.1> <EMI ID=50.1><EMI ID=51.1><EMI ID=52.1><EMI ID=53.1><EMI ID=54.1><EMI ID=55.1><EMI ID=56.1><EMI ID=57.1>R et n ont les significations définies.<EMI ID=58.1><EMI ID=59.1><EMI ID=60.1><EMI ID=61.1><EMI ID=62.1> 5,- Conposés préparés par le procédé suivant . l'une ou l'autre des revendications' 1 et 2.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP46037202A JPS5029471B1 (fr) | 1971-05-30 | 1971-05-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE773937A true BE773937A (fr) | 1972-04-14 |
Family
ID=12490981
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE773937A BE773937A (fr) | 1971-05-30 | 1971-10-14 | Procede de preparation d'aroyl-alkyl-piperidines |
Country Status (2)
| Country | Link |
|---|---|
| JP (1) | JPS5029471B1 (fr) |
| BE (1) | BE773937A (fr) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS53110772U (fr) * | 1977-02-12 | 1978-09-04 | ||
| JPS5458317U (fr) * | 1977-09-12 | 1979-04-23 | ||
| JP3004327U (ja) * | 1994-02-02 | 1994-11-15 | 隆典 森 | ひも付きごみ袋 |
-
1971
- 1971-05-30 JP JP46037202A patent/JPS5029471B1/ja active Pending
- 1971-10-14 BE BE773937A patent/BE773937A/fr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5029471B1 (fr) | 1975-09-23 |
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