SU462333A3 - Способ получени замещенных пиперидинов - Google Patents
Способ получени замещенных пиперидиновInfo
- Publication number
- SU462333A3 SU462333A3 SU1840861A SU1840861A SU462333A3 SU 462333 A3 SU462333 A3 SU 462333A3 SU 1840861 A SU1840861 A SU 1840861A SU 1840861 A SU1840861 A SU 1840861A SU 462333 A3 SU462333 A3 SU 462333A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- parts
- bis
- fluorophenyl
- evaporated
- residue
- Prior art date
Links
- 150000003053 piperidines Chemical class 0.000 title description 2
- 238000004519 manufacturing process Methods 0.000 title 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 239000000203 mixture Substances 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- JFRQXVVTMRETBH-UHFFFAOYSA-N 4,4-bis(4-fluorophenyl)butanoyl chloride Chemical compound C1=CC(F)=CC=C1C(CCC(Cl)=O)C1=CC=C(F)C=C1 JFRQXVVTMRETBH-UHFFFAOYSA-N 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 238000010828 elution Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- UOBOSSRBVANWMD-UHFFFAOYSA-N 4-(4-fluorophenyl)-4-hydroxybutanoic acid Chemical compound OC(=O)CCC(O)C1=CC=C(F)C=C1 UOBOSSRBVANWMD-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- QHPIVNMZWWJPGE-UHFFFAOYSA-N 1-(2-methylphenyl)piperidin-4-ol Chemical compound CC1=CC=CC=C1N1CCC(O)CC1 QHPIVNMZWWJPGE-UHFFFAOYSA-N 0.000 description 1
- DHZXAHNUFDZTEF-UHFFFAOYSA-N 2,2-bis(4-fluorophenyl)butanoic acid Chemical compound FC1=CC=C(C=C1)C(C(=O)O)(CC)C1=CC=C(C=C1)F DHZXAHNUFDZTEF-UHFFFAOYSA-N 0.000 description 1
- BYNBAMHAURJNTR-UHFFFAOYSA-N 3-piperidin-4-yl-1h-benzimidazol-2-one Chemical compound O=C1NC2=CC=CC=C2N1C1CCNCC1 BYNBAMHAURJNTR-UHFFFAOYSA-N 0.000 description 1
- CZNWJIAAVVXYFS-UHFFFAOYSA-N 4,4-bis(4-fluorophenyl)butanoic acid Chemical compound C=1C=C(F)C=CC=1C(CCC(=O)O)C1=CC=C(F)C=C1 CZNWJIAAVVXYFS-UHFFFAOYSA-N 0.000 description 1
- -1 4,4-bis- (l-fluorophenyl) -3-butenoic acid Chemical compound 0.000 description 1
- LZAYOZUFUAMFLD-UHFFFAOYSA-N 4-(4-chlorophenyl)-4-hydroxypiperidine Chemical compound C=1C=C(Cl)C=CC=1C1(O)CCNCC1 LZAYOZUFUAMFLD-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D307/32—Oxygen atoms
- C07D307/33—Oxygen atoms in position 2, the oxygen atom being in its keto or unsubstituted enol form
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/52—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen
- C07C57/58—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/64—Acyl halides
- C07C57/72—Acyl halides containing six-membered aromatic rings
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9485771A JPS5527915B2 (enrdf_load_stackoverflow) | 1971-11-25 | 1971-11-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU462333A3 true SU462333A3 (ru) | 1975-02-28 |
Family
ID=14121686
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1840861A SU462333A3 (ru) | 1971-11-25 | 1972-10-24 | Способ получени замещенных пиперидинов |
Country Status (14)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4082755A (en) * | 1977-02-14 | 1978-04-04 | Janssen Pharmaceutica N.V. | 1-[(Diarylmethyl)aminoalkyl]piperidimes |
| CN106187863A (zh) * | 2016-07-15 | 2016-12-07 | 湖南中南制药有限责任公司 | 五氟利多的制备方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE633495A (enrdf_load_stackoverflow) * | 1962-06-13 |
-
1971
- 1971-11-25 JP JP9485771A patent/JPS5527915B2/ja not_active Expired
-
1972
- 1972-10-06 AR AR244512A patent/AR198393A1/es active
- 1972-10-12 BG BG021601A patent/BG20348A3/xx unknown
- 1972-10-12 BG BG024007A patent/BG20349A3/xx unknown
- 1972-10-24 SU SU1840861A patent/SU462333A3/ru active
- 1972-10-25 CA CA154,791A patent/CA983503A/en not_active Expired
- 1972-11-03 NL NL7214913A patent/NL7214913A/xx not_active Application Discontinuation
- 1972-11-09 CH CH1629172A patent/CH579048A5/xx not_active IP Right Cessation
- 1972-11-22 RO RO7200081658A patent/RO63063A/ro unknown
- 1972-11-22 RO RO7200072900A patent/RO62760A/ro unknown
- 1972-11-23 FR FR7241668A patent/FR2161007A1/fr active Granted
- 1972-11-23 ES ES408926A patent/ES408926A1/es not_active Expired
- 1972-11-23 YU YU2916/72A patent/YU35120B/xx unknown
- 1972-11-24 CS CS8036A patent/CS168014B2/cs unknown
- 1972-11-24 IL IL40917A patent/IL40917A/en unknown
- 1972-11-24 HU HUJA673A patent/HU165208B/hu unknown
-
1973
- 1973-10-22 AR AR250627A patent/AR199497A1/es active
Also Published As
| Publication number | Publication date |
|---|---|
| CA983503A (en) | 1976-02-10 |
| FR2161007B1 (enrdf_load_stackoverflow) | 1976-03-05 |
| BG20349A3 (bg) | 1975-11-05 |
| JPS4860092A (enrdf_load_stackoverflow) | 1973-08-23 |
| HU165208B (enrdf_load_stackoverflow) | 1974-07-27 |
| IL40917A0 (en) | 1973-01-30 |
| YU291672A (en) | 1980-03-15 |
| AR199497A1 (es) | 1974-09-09 |
| YU35120B (en) | 1980-09-25 |
| ES408926A1 (es) | 1976-03-01 |
| CS168014B2 (enrdf_load_stackoverflow) | 1976-05-28 |
| RO62760A (fr) | 1978-02-15 |
| AR198393A1 (es) | 1974-06-21 |
| FR2161007A1 (en) | 1973-07-06 |
| CH579048A5 (enrdf_load_stackoverflow) | 1976-08-31 |
| NL7214913A (enrdf_load_stackoverflow) | 1973-05-29 |
| RO63063A (fr) | 1978-07-15 |
| BG20348A3 (bg) | 1975-11-05 |
| JPS5527915B2 (enrdf_load_stackoverflow) | 1980-07-24 |
| IL40917A (en) | 1976-10-31 |
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