SU432717A3 - Способ получения солей инденопиридина - Google Patents

Способ получения солей инденопиридина

Info

Publication number: SU432717A3
Authority: SU; USSR - Soviet Union
Prior art keywords: indeno; hydrochloride; hexahydro; pyridin; acid
Prior art date: 1971-01-21

Application number

SU1740382A

Other languages

English (en)

Russian (ru)

Original Assignee

Ипостранцы Жан Мишель Бастиан, 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.)

1971-01-21

Filing date

1972-01-20

Publication date

1974-06-15

1972-01-20 Application filed by Ипостранцы Жан Мишель Бастиан, Антон Эбнетер , Эрвин Рисси, Иностранна фирма filed Critical Ипостранцы Жан Мишель Бастиан, Антон Эбнетер , Эрвин Рисси

1974-06-15 Application granted granted Critical

1974-06-15 Publication of SU432717A3 publication Critical patent/SU432717A3/ru

Links

238000000034 method Methods 0.000 title description 18
PFWJFKBTIBAASX-UHFFFAOYSA-N 9h-indeno[2,1-b]pyridine Chemical class C1=CN=C2CC3=CC=CC=C3C2=C1 PFWJFKBTIBAASX-UHFFFAOYSA-N 0.000 title description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 45
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 15
239000002253 acid Substances 0.000 description 15
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
150000003839 salts Chemical class 0.000 description 10
150000001875 compounds Chemical class 0.000 description 9
238000000354 decomposition reaction Methods 0.000 description 8
-1 trichloroacetic acid Chemical class 0.000 description 8
239000000203 mixture Substances 0.000 description 7
239000000047 product Substances 0.000 description 7
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
150000007513 acids Chemical class 0.000 description 6
125000000217 alkyl group Chemical group 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
229930040373 Paraformaldehyde Natural products 0.000 description 4
238000009835 boiling Methods 0.000 description 4
FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 4
239000000460 chlorine Chemical group 0.000 description 4
229910052801 chlorine Inorganic materials 0.000 description 4
229920002866 paraformaldehyde Polymers 0.000 description 4
KRIOVPPHQSLHCZ-UHFFFAOYSA-N propiophenone Chemical compound CCC(=O)C1=CC=CC=C1 KRIOVPPHQSLHCZ-UHFFFAOYSA-N 0.000 description 4
UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 4
238000010992 reflux Methods 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
229910052794 bromium Inorganic materials 0.000 description 3
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 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
125000000753 cycloalkyl group Chemical group 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
229910052731 fluorine Inorganic materials 0.000 description 2
239000011737 fluorine Substances 0.000 description 2
125000001153 fluoro group Chemical group F* 0.000 description 2
150000003840 hydrochlorides Chemical class 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
238000005245 sintering Methods 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
ZDPAWHACYDRYIW-UHFFFAOYSA-N 1-(4-fluorophenyl)ethanone Chemical compound CC(=O)C1=CC=C(F)C=C1 ZDPAWHACYDRYIW-UHFFFAOYSA-N 0.000 description 1
SCJISYUIPXMQAB-UHFFFAOYSA-N 1-phenylpropan-1-one;hydrochloride Chemical compound Cl.CCC(=O)C1=CC=CC=C1 SCJISYUIPXMQAB-UHFFFAOYSA-N 0.000 description 1
AYJJTPLDSZAGGA-UHFFFAOYSA-N 2-ethyl-7-methyl-5-(4-methylphenyl)-1,3,4,4a,5,9b-hexahydroindeno[1,2-c]pyridine Chemical class C1N(CC)CCC2C1C1=CC=C(C)C=C1C2C1=CC=C(C)C=C1 AYJJTPLDSZAGGA-UHFFFAOYSA-N 0.000 description 1
ATOOHBIWRYLVIE-UHFFFAOYSA-N 2-methoxy-1-phenylpropan-1-one Chemical compound COC(C)C(=O)C1=CC=CC=C1 ATOOHBIWRYLVIE-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
239000012359 Methanesulfonyl chloride Substances 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
229940092714 benzenesulfonic acid Drugs 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
CODNYICXDISAEA-UHFFFAOYSA-N bromine monochloride Chemical compound BrCl CODNYICXDISAEA-UHFFFAOYSA-N 0.000 description 1
GMBHLHMRHUMBHU-UHFFFAOYSA-N butan-2-one;hydrochloride Chemical compound Cl.CCC(C)=O GMBHLHMRHUMBHU-UHFFFAOYSA-N 0.000 description 1
239000001273 butane Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
239000012024 dehydrating agents‎ Substances 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
DZGCGKFAPXFTNM-UHFFFAOYSA-N ethanol;hydron;chloride Chemical compound Cl.CCO DZGCGKFAPXFTNM-UHFFFAOYSA-N 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hcl hcl Chemical compound Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
229940071870 hydroiodic acid Drugs 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
238000002955 isolation Methods 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
230000005012 migration Effects 0.000 description 1
238000013508 migration Methods 0.000 description 1
239000011707 mineral Substances 0.000 description 1
229940075566 naphthalene Drugs 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
PJGSXYOJTGTZAV-UHFFFAOYSA-N pinacolone Chemical compound CC(=O)C(C)(C)C PJGSXYOJTGTZAV-UHFFFAOYSA-N 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000008707 rearrangement Effects 0.000 description 1
230000007017 scission Effects 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/06—Ring systems of three rings
- C07D221/16—Ring systems of three rings containing carbocyclic rings other than six-membered

Landscapes

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

SU1740382A 1971-01-21 1972-01-20 Способ получения солей инденопиридина SU432717A3 (ru)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH88971		1971-01-21

Publications (1)

Publication Number	Publication Date
SU432717A3 true SU432717A3 (ru)	1974-06-15

Family

ID=4197536

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SU1740382A SU432717A3 (ru)	1971-01-21	1972-01-20	Способ получения солей инденопиридина

Country Status (6)

Country	Link
AT (1)	ATA47072A (de)
CH (1)	CH546764A (de)
ES (1)	ES399021A1 (de)
GB (1)	GB1382662A (de)
SU (1)	SU432717A3 (de)
ZA (1)	ZA72437B (de)

1971
- 1971-01-21 CH CH88971A patent/CH546764A/de not_active IP Right Cessation
1972
- 1972-01-17 GB GB3054674A patent/GB1382662A/en not_active Expired
- 1972-01-19 ES ES399021A patent/ES399021A1/es not_active Expired
- 1972-01-20 AT AT47072*#A patent/ATA47072A/de not_active IP Right Cessation
- 1972-01-20 SU SU1740382A patent/SU432717A3/ru active
- 1972-01-21 ZA ZA720437A patent/ZA72437B/xx unknown

Also Published As

Publication number	Publication date
ZA72437B (en)	1973-09-26
ATA47072A (de)	1975-04-15
GB1382662A (en)	1975-02-05
ES399021A1 (es)	1975-05-16
CH546764A (de)	1974-03-15

Publication	Publication Date	Title
SU856383A3 (ru)	1981-08-15	Способ получени производных 1-(N-пиперидино)фталазина или их солей
SU446963A1 (ru)	1974-10-15	Способ получени и - изомеров фенилалканоламинов
JPH0314315B2 (de)	1991-02-26
US3940404A (en)	1976-02-24	2-Substituted phenyl-6-trifluoromethyl-4-pyridyl-carbinolamines
US3953463A (en)	1976-04-27	2-Aryl-6-trifluoromethyl-4-pyridyl-carbinolamine antimalarials
US3309370A (en)	1967-03-14	Bicycloalkyl piperazine derivatives and process
SU664564A3 (ru)	1979-05-25	Способ получени производных фенилпиперазина или их солей
SU432717A3 (ru)	1974-06-15	Способ получения солей инденопиридина
US3886167A (en)	1975-05-27	2-Aryl-6-trifluoromethyl-4-pyridylcarbinolamine antimalarials
US2695290A (en)	1954-11-23	Derivatives of indole and method for the production thereof
SU592350A3 (ru)	1978-02-05	Способ получени производных бутирофенона или их солей
US2686784A (en)	1954-08-17	Piperidine derivatives
US5663350A (en)	1997-09-02	Process for the preparation of intermediates useful for the synthesis of histamine receptor antagonists
US3156697A (en)	1964-11-10	Pyridylcoumarins
JPS584020B2 (ja)	1983-01-24	シンキナイソキノリンルイ
US4218455A (en)	1980-08-19	1-(4-Fluorophenyl)-4-[1,2,3,6-tetrahydro-4-(phenylthio)-1-pyridinyl]-butanones and related sulfoxides and sulfones
Whitmore et al.	1945	Heterocyclic Basic Compounds. I. 2-Aminoalkylamino-pyridines1
NO130329B (de)	1974-08-12
US2785166A (en)	1957-03-12	Ethers of heterocyclic alcohols and tetrahydroisoquinolinealkanols, their salts and methods for their production
SU422146A3 (de)	1974-03-30
US3632816A (en)	1972-01-04	6-chloroimidazo(2 1-b)thiazole and its 5-substituted derivatives
SU449485A3 (ru)	1974-11-05	Способ получени -замещенных сложных эфиров 1,2,3,6-тетрагидро-4пиридилметилкарбоновой кислоты
US4085102A (en)	1978-04-18	2-Amino-8-arylideno-3,4,5,6,7,8-hexahydro-4-arlypyrido[4,3-d]pyrimidines
SU414790A3 (ru)	1974-02-05	СПОСОБ ПОЛУЧЕНИЯ ПРОИЗВОДНЫХ 2,3-ДИГИДРО-5Н-ИМИДАЗО[2,1-о]ИЗОИНДОЛА12
US4267318A (en)	1981-05-12	1-(Diarylmethyl)-4-piperidinamine and derivatives thereof