SU520914A3 - Method for preparing benzocycloheptatiophenone derivatives or their salts - Google Patents
Method for preparing benzocycloheptatiophenone derivatives or their saltsInfo
- Publication number
- SU520914A3 SU520914A3 SU2017993A SU2017993A SU520914A3 SU 520914 A3 SU520914 A3 SU 520914A3 SU 2017993 A SU2017993 A SU 2017993A SU 2017993 A SU2017993 A SU 2017993A SU 520914 A3 SU520914 A3 SU 520914A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- salts
- benzocycloheptatiophenone
- derivatives
- preparing
- piperidylidene
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
-
- 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
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/08—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing alicyclic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Description
или их солей, заключающийс в том, что соединение общей формулы ц где R имеет указанные выше значени и оксогруппа находитс в положении 9 или iO, подвергают взаимодейсгвию с соединением общей формулы Щ где R, и R, имеют указанные выше зна чени и Hal означает галоген, с последую щим выделением целевого продукта в виде основани или соли. Если R - галоген, то он, в частности означает хлор или бром. Если Rj означае-т галоген, -то он, в частности, означает фтор хлор или бром. В качестве галоидных заме тителей дл фенильного остатка R. можно использовать, в частности, фтор, хлор или бром. Взаимодействие соединений формулы Ц с соединени ми формулы 111 можно осущест вл ть, например, в инертном при услови х реакции органическом растворителе и пред почтительно в присутствии основани , напр мер карбоната натри или кали , Вь хздным вл етс применение сильно пол рного рас ворител , например гексаметилтриамида фос форной кислоты, диметилсульфоксида, димеметилформамида и т.д. Температуру процесса желательно поддерживать низкой, например, обычно межд комнатной и GO С. Из свободных оснований известными способами можно получать соли и, наоборот, из солей получать свободкые основани . Обычно получаюТ хлоргидраты или бромгидфаты. Пример 1, 4.(l -бензил-4-пиперидилиден )-4Н-бензо ,5} циклогепта Il,2-bl тиофен-1О(9Н)-он 11,6 г 4-(4 пиперидилиден)-4Н-бензо 4,5 диклогепта fl,2-bj тиофен-1О (9Н)-она в виде основани , 12,5 г безводной соды в 12О мл гексаметилтриамида фосфорной кислоты при температуре 25 С смещи ваю-т с 6 г бензихжпорида. После восемнадцатнчасового перемешивани при комнатной температуре перемешивают еще в течение часа при 5 О С. Затем реакционную смесь разбавл ют J. л воды и экстрагируют основание 5ОО мл бензола. Бензольный раствор концентрируют и остаток перекристаллизовы- вают из изодронанола. Получают 4-(1-бензил-4-пиперидилиден )4Н-бензо 4,5 uwKлогепта 1,2-Ь гиофен-1О{9Н)-она с т.пл. 136-138°а Пример 2. 4-(l-Хлорбензил-4-пиперидилиден )-4Н-бензо 4,53 циклогепта С1,2-Ъ}тиофен-1О( 9П)-он. 5,17 г 4-(4-пиперидилиден)-4Н-бензо 4,51 циклогепта l ,2- ЬЗтиофен-1О (9Н )-она в виде основани , 5,56 г безводной соды в 60 мл гексаметилтриамида фосфорной кислоты при 2О-25 С смешивают с 3,38 г п-хлорбензилхлоридом. После восем- надцатичасового размешивани при комнатной температуре реакционную смесь разбав/ 1 ют 5ОО мл воды и основание экстрагируют 35О мл бензола. Бензольный раствор концентрируют и остаток раствор ют в 30мл абсолютного этанола. К этому раствору добавл юТ этанольный раствор хлористого водорода до слабокислой реакции и гидрохлорид после выдерживани в течение ночи при О-5 С отфильтровывают и перекристаллизовывают из 85%-ного этанола. Получают 4- - (1 -П -хлорбензил--4 -пиперидилиден)-4Н- -бензо 4,5 3 циклогепта l, 2- Ъ тиофен- О (9Н)он-гидрохлорид с т. пл. 269-273°С (с разложением). Пример 3. 4-(1-Дифенилметил-4-пиперидилиден )-4Н-бензо 4,5} циклогепта 1,2-ЪЗтиофен-1О(9Н)-он. К смеси 1,8 г безводного карбоната натри и 3,Ог4-( 4-пиперидилиден)-4Н-бензо 4,5 циклогепта 1,2-6 тиофен-10( 9Н)-она в 15 мл диметилформамида прибавл ют по капл м 2,8 мл дифенилхлорметана при комнатной температуре. Реакционную смесь перемешивают в течение 4,5 час при ТО С, охлажor a salt thereof, consisting in that the compound of the general formula i, where R has the above values and the oxo group is in the 9 or iO position, is reacted with the compound of the general formula Y, where R and R, have the above values and Hal is halogen followed by isolation of the desired product as a base or salt. If R is halogen, then it means in particular chlorine or bromine. If Rj means halogen, it means, in particular, fluorine chlorine or bromine. Fluorine, chlorine or bromine may be used as the halogen substituents for the phenyl residue R. The compounds of the formula C with the compounds of the formula 111 can be reacted, for example, in an organic solvent which is inert under the reaction conditions, and preferably in the presence of a base, for example sodium or potassium carbonate, a highly polar solvent, for example phosphoric acid hexamethyltriamide, dimethyl sulfoxide, dimethylformamide, etc. The process temperature should preferably be kept low, for example, usually between room and GO C. Salts can be obtained from free bases by known methods and, conversely, free bases can be obtained from salts. Usually I get chlorohydrates or bromhydates. Example 1, 4. (l-benzyl-4-piperidylidene) -4H-benzo, 5} cyclohepta Il, 2-bl thiophene-1O (9H) -one 11.6 g 4- (4 piperidylidene) -4H-benzo 4 , 5 diclopeta fl, 2-bj thiophene-1O (9H) -one as a base, 12.5 g of anhydrous soda in 12O ml of hexamethylphosphoric acid at 25 ° C mixed with 6 g of benzichjporide. After eighteen hour stirring at room temperature, the mixture is stirred for another hour at 5 ° C. The reaction mixture is then diluted with J. l of water and the base is extracted with 5OO ml of benzene. The benzene solution is concentrated and the residue is recrystallized from isodronanol. 4- (1-benzyl-4-piperidylidene) 4H-benzo 4,5 uwKlopepta 1,2-b giofen-1O {9H) -one is obtained with m.p. 136-138 ° a. Example 2. 4- (l-Chlorobenzyl-4-piperidylidene) -4H-benzo 4.53 cyclohepta C1,2-b} thiophene-1O (9P) -one. 5.17 g of 4- (4-piperidylidene) -4H-benzo 4.51 cyclohepta l, 2-hStiofen-1O (9H) -one as a base, 5.56 g of anhydrous soda in 60 ml of hexamethyltriamide phosphoric acid at 2O- 25 C is mixed with 3.38 g of p-chlorobenzyl chloride. After stirring for eighteen hours at room temperature, the reaction mixture is diluted with 1 x 5OO ml of water and the base is extracted with 35 O ml of benzene. The benzene solution is concentrated and the residue is dissolved in 30 ml of absolute ethanol. An ethanolic solution of hydrogen chloride is added to this solution until a weakly acidic reaction and the hydrochloride, after keeping overnight at 0-5 ° C, is filtered and recrystallized from 85% ethanol. 4- - (1 -P-chlorobenzyl-4-piperidylidene) -4H- -benzo 4,5 3 cyclohepta l, 2- ти thiophene-O (9H) on-hydrochloride is obtained with m.p. 269-273 ° С (with decomposition). Example 3. 4- (1-Diphenylmethyl-4-piperidylidene) -4H-benzo 4,5} cyclohepta 1,2-b, Thiophene-1O (9H) -one. To a mixture of 1.8 g of anhydrous sodium carbonate and 3, Og4- (4-piperidylidene) -4H-benzo 4,5 cyclohepta 1,2-6 thiophene-10 (9H) -one in 15 ml of dimethylformamide is added dropwise 2 , 8 ml of diphenylchloromethane at room temperature. The reaction mixture is stirred for 4.5 hours at TO, cooled.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH98672A CH569012A5 (en) | 1972-01-24 | 1972-01-24 | 4-piperidylidene benzocycloheptathiophenes - - antihistamines and serotonin and acetyl choline inhibitors |
Publications (1)
Publication Number | Publication Date |
---|---|
SU520914A3 true SU520914A3 (en) | 1976-07-05 |
Family
ID=4199812
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
SU2017993A SU520914A3 (en) | 1972-01-24 | 1974-04-23 | Method for preparing benzocycloheptatiophenone derivatives or their salts |
Country Status (6)
Country | Link |
---|---|
JP (1) | JPS5817756B2 (en) |
CH (1) | CH569012A5 (en) |
CS (1) | CS179977B2 (en) |
ES (1) | ES438598A1 (en) |
SE (1) | SE423712B (en) |
SU (1) | SU520914A3 (en) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS649343U (en) * | 1987-07-07 | 1989-01-19 |
-
1972
- 1972-01-24 CH CH98672A patent/CH569012A5/en not_active IP Right Cessation
-
1973
- 1973-01-23 CS CS7300000504A patent/CS179977B2/en unknown
-
1974
- 1974-04-23 SU SU2017993A patent/SU520914A3/en active
-
1975
- 1975-06-16 ES ES438598A patent/ES438598A1/en not_active Expired
-
1976
- 1976-01-13 SE SE7600275A patent/SE423712B/en unknown
-
1980
- 1980-12-11 JP JP55175690A patent/JPS5817756B2/en not_active Expired
Also Published As
Publication number | Publication date |
---|---|
JPS57112390A (en) | 1982-07-13 |
ES438598A1 (en) | 1977-05-16 |
CH569012A5 (en) | 1975-11-14 |
AU5137773A (en) | 1974-07-25 |
SE7600275L (en) | 1976-01-13 |
CS179977B2 (en) | 1977-12-30 |
SE423712B (en) | 1982-05-24 |
JPS5817756B2 (en) | 1983-04-09 |
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