SU423295A3 - Способ получения производных фенилпиперидина или их солей - Google Patents

Способ получения производных фенилпиперидина или их солей

Info

Publication number: SU423295A3
Authority: SU; USSR - Soviet Union
Prior art keywords: benzoyl; hydroxy; methyl; solution; salts
Prior art date: 1970-12-04

Application number

SU1765202A

Other languages

English (en)

Russian (ru)

Original Assignee

Иностранцы Антон Эбнетер , Эрвин Рисси

Иностранна фирма

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1970-12-04

Filing date

1971-04-08

Publication date

1974-04-05

1971-04-08 Application filed by Иностранцы Антон Эбнетер , Эрвин Рисси, Иностранна фирма filed Critical Иностранцы Антон Эбнетер , Эрвин Рисси

1974-04-05 Application granted granted Critical

1974-04-05 Publication of SU423295A3 publication Critical patent/SU423295A3/ru

Links

150000003839 salts Chemical class 0.000 title description 4
238000004519 manufacturing process Methods 0.000 title 1
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
239000000047 product Substances 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
238000000034 method Methods 0.000 description 4
239000000203 mixture Substances 0.000 description 4
NKEJNNRTXMYMTR-UHFFFAOYSA-N (4-hydroxy-3-phenylpiperidin-4-yl)-phenylmethanone Chemical compound C(C1=CC=CC=C1)(=O)C1(C(CNCC1)C1=CC=CC=C1)O NKEJNNRTXMYMTR-UHFFFAOYSA-N 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
229910052943 magnesium sulfate Inorganic materials 0.000 description 3
235000019341 magnesium sulphate Nutrition 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
JUYSZZMOSLZFCF-UHFFFAOYSA-N (4-bromo-1-methyl-3-phenylpiperidin-4-yl)-phenylmethanone hydrobromide Chemical compound Br.C(C1=CC=CC=C1)(=O)C1(C(CN(CC1)C)C1=CC=CC=C1)Br JUYSZZMOSLZFCF-UHFFFAOYSA-N 0.000 description 2
GADCSODZDASQJN-UHFFFAOYSA-N (4-hydroxy-1-methyl-3-phenylpiperidin-4-yl)-phenylmethanone Chemical compound C(C1=CC=CC=C1)(=O)C1(C(CN(CC1)C)C1=CC=CC=C1)O GADCSODZDASQJN-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
239000002585 base Substances 0.000 description 2
238000009835 boiling Methods 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
238000001816 cooling Methods 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
-1 ethyl 4-acetoxy-4-benzoyl-3 - phenylpiperidinecarboxylic acid Chemical compound 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
238000010992 reflux Methods 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
QZNMGHHMQOWYCW-UHFFFAOYSA-N (1-methyl-3-phenylpiperidin-4-yl)-phenylmethanone hydrobromide Chemical compound Br.C(C1=CC=CC=C1)(=O)C1C(CN(CC1)C)C1=CC=CC=C1 QZNMGHHMQOWYCW-UHFFFAOYSA-N 0.000 description 1
PYNBGTIFODDTRW-UHFFFAOYSA-N (4-benzoyl-1-methyl-3-phenylpiperidin-4-yl) acetate Chemical compound CN1CCC(OC(C)=O)(C(C1)C1=CC=CC=C1)C(=O)C1=CC=CC=C1 PYNBGTIFODDTRW-UHFFFAOYSA-N 0.000 description 1
PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 1
NKOGCJIYHZVBDR-UHFFFAOYSA-N 1-phenylpiperidin-2-one Chemical class O=C1CCCCN1C1=CC=CC=C1 NKOGCJIYHZVBDR-UHFFFAOYSA-N 0.000 description 1
LLSKXGRDUPMXLC-UHFFFAOYSA-N 1-phenylpiperidine Chemical class C1CCCCN1C1=CC=CC=C1 LLSKXGRDUPMXLC-UHFFFAOYSA-N 0.000 description 1
GELKGHVAFRCJNA-UHFFFAOYSA-N 2,2-Dimethyloxirane Chemical compound CC1(C)CO1 GELKGHVAFRCJNA-UHFFFAOYSA-N 0.000 description 1
KFZMGEQAYNKOFK-UHFFFAOYSA-N 2-propanol Substances CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
XHCBQTXBNRTCOU-UHFFFAOYSA-N CCOC(=O)C1=C(CN(C=C1)C)C2=CC=CC=C2 Chemical compound CCOC(=O)C1=C(CN(C=C1)C)C2=CC=CC=C2 XHCBQTXBNRTCOU-UHFFFAOYSA-N 0.000 description 1
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
OILDMJUOPPBLHN-UHFFFAOYSA-N [4-hydroxy-1-(2-hydroxy-2-methylpropyl)-3-phenylpiperidin-4-yl]-phenylmethanone Chemical compound C(C1=CC=CC=C1)(=O)C1(C(CN(CC1)CC(C)(O)C)C1=CC=CC=C1)O OILDMJUOPPBLHN-UHFFFAOYSA-N 0.000 description 1
ZYQRQLOOSVFLBC-UHFFFAOYSA-N [4-hydroxy-1-(2-hydroxyethyl)-3-phenylpiperidin-4-yl]-phenylmethanone Chemical compound C(C1=CC=CC=C1)(=O)C1(C(CN(CC1)CCO)C1=CC=CC=C1)O ZYQRQLOOSVFLBC-UHFFFAOYSA-N 0.000 description 1
229960000583 acetic acid Drugs 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 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
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
238000006073 displacement reaction Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
YKWNUSJLICDQEO-UHFFFAOYSA-N ethoxyethane;propan-2-ol Chemical compound CC(C)O.CCOCC YKWNUSJLICDQEO-UHFFFAOYSA-N 0.000 description 1
VHHAMVPFHQZXNQ-UHFFFAOYSA-N ethyl 4-acetyloxy-4-benzoyl-3-phenylpiperidine-1-carboxylate Chemical compound CCOC(=O)N1CCC(OC(C)=O)(C(C1)C1=CC=CC=C1)C(=O)C1=CC=CC=C1 VHHAMVPFHQZXNQ-UHFFFAOYSA-N 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000000284 extract Substances 0.000 description 1
239000012458 free base Substances 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229910000042 hydrogen bromide Inorganic materials 0.000 description 1
239000005457 ice water Substances 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical class II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
238000002955 isolation Methods 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
229940051803 opioid analgesics phenylpiperidine derivative Drugs 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000009938 salting Methods 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000126 substance 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
- C07D211/08—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
- C07D211/18—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 substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/30—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 substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom
- C07D211/32—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 substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom by oxygen atoms
- 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
- C07D211/38—Halogen atoms or nitro radicals
- 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
- C07D211/48—Oxygen atoms attached in position 4 having an acyclic carbon atom attached in position 4
- C07D211/50—Aroyl radical

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Hydrogenated Pyridines (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

SU1765202A 1970-12-04 1971-04-08 Способ получения производных фенилпиперидина или их солей SU423295A3 (ru)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH1793970A CH542207A (de)	1970-12-04	1970-12-04	Verfahren zur Herstellung neuer Phenylpiperidinderivate

Publications (1)

Publication Number	Publication Date
SU423295A3 true SU423295A3 (ru)	1974-04-05

Family

ID=4429225

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SU1765202A SU423295A3 (ru)	1970-12-04	1971-04-08	Способ получения производных фенилпиперидина или их солей

Country Status (3)

Country	Link
BG (1)	BG19152A3 (de)
CH (1)	CH542207A (de)
SU (1)	SU423295A3 (de)

1970
- 1970-12-04 CH CH1793970A patent/CH542207A/de not_active IP Right Cessation
1971
- 1971-04-07 BG BG019908A patent/BG19152A3/xx unknown
- 1971-04-08 SU SU1765202A patent/SU423295A3/ru active

Also Published As

Publication number	Publication date
CH542207A (de)	1973-09-30
BG19152A3 (bg)	1975-04-30

Publication	Publication Date	Title
SU552025A3 (ru)	1977-03-25	Способ получени производных фенил-имидазолил-алканов
SU867298A3 (ru)	1981-09-23	Способ получени производных пиперидина или их солей
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SU513624A3 (ru)	1976-05-05	Способ получени производных 2-пиперазинил-тиазола
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US3530137A (en)	1970-09-22	Certain alkyl and aryl ethers and thioethers of tropine and derivatives thereof
SU535899A3 (ru)	1976-11-15	Способ получени -(1-бисарилалкиламиноалкил)-аралкоксибензиловых спиртов или их солей, рацематов или оптически активных антиподов
EP0142754A2 (de)	1985-05-29	2-Substituierte, eine Imidazolylgruppe tragende Benzoesäuren, Verfahren zu ihrer Herstellung und sie enthaltende pharmazeutische Zubereitungen
US3270028A (en)	1966-08-30	Certain 3-aryl-1, 2, 4-oxadiazoles
SU795487A3 (ru)	1981-01-07	Способ получени производных геллебри-гЕНиНА или иХ СОлЕй
SU470960A3 (ru)	1975-05-15	Способ получени производных 3-амино-2-пиразолина
US3228961A (en)	1966-01-11	Diethylamino and pyrrolidino lower alkyl esters of 3, 5-dimethoxy-4-butoxy and amyloxy benzoic acids
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SU512712A3 (ru)	1976-04-30	Способ получени 1,4-дизамещенных пиперазинов
SU474149A3 (ru)	1975-06-14	Способ получени производных 2,3,5,6-тетрагидроимидазо(2,1-в) тиазола
SU422144A3 (ru)	1974-03-30	Способ получения производных фенилпиперидина или их солей