SU656511A3 - Method of obtaining derivatives of hexahydro-4-indolinole and salts thereof - Google Patents
Method of obtaining derivatives of hexahydro-4-indolinole and salts thereofInfo
- Publication number
- SU656511A3 SU656511A3 SU772472892A SU2472892A SU656511A3 SU 656511 A3 SU656511 A3 SU 656511A3 SU 772472892 A SU772472892 A SU 772472892A SU 2472892 A SU2472892 A SU 2472892A SU 656511 A3 SU656511 A3 SU 656511A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- hexahydro
- salts
- indolinole
- obtaining derivatives
- methylene chloride
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
-
- 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
- A61P25/24—Antidepressants
-
- 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
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Psychiatry (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
менении соответствующего с6, р -эпоксида в качестве алкилирующего агента и проведении реакции при (-10)-100°С Целевые соединени MoiVx находить с в свободном состо нии в виде осно вани или в виде аддитивных солей с кислотами. Из свободных оснований могут быть известным способом получены кислые аддитивные соли, в частности гидромаЛеинат или гидромалонат и наоборот Пример. (3aRS 4SR, 7aRS)-4- (3, 4-Дихлорф енил)-гексагидро-1- - (2-оксиэтил)-4- индолинол. 3,8 г (3aRS, 4SR, 7aRS)-4-(3,4-дихлорфенил )-гексагидро-4-индолинол 1,6 г 2-бромэтанола и 4 г- карбоната натри нагревают в 50 мл диметилформ амида в течение 4ч до 100°С. Полученную суспензию упаривают, остаток обрабатывают метиленхлоридом и 2 и,, винной кислотой. Водную фазу подщела чивают и экстрагируют метиленхлоридо Метиленхлоридную фазу отдел ют, сушат над сульфатом натри , упаривают и к масл нистому остатку Добавл ют эквивалентное количество малоновой кислоты. Гидромалонат кристаллизуют из смеси этилацетат-этанол, т.пл. . Исходное вещество получают следую щим образом. 3,4-Дихлорфенилмагнийбромид (получен из 4,2 г магни и 38,5 г 1-бром-3 ,4-дихлорбензола) обрабатываю 26,4 г этилового эфира цис-пергидро14 -4-оксо-1-индолинкарбоновой кислоты в300 мл тетрагидрофурана, перемешивают 4 ч при комнатной температуре, смешивают с 100 мл 2 н. сол ной кис-, лоты и 200. мл эфира. Органическую фазу промывают водой, сушат над сульфатом натри , удал ют эфир и получают этиловый эфир (3aRS, 4SR, 7aRS)-4- (3,4-дихлорфенил)-гексагидро-4-окси- 1-индолинкарбоновой кислоты в виде масл нистого продукта, который непосредственно подвергают дальнейшей переработке. 24,9 г синтезированного эфира раствор ют в 240 мл метаНола, до бавл ют 240 мл Юн. едкого натра и перемешивают 15 ч при температуре кипени . После охлаждени экстрагируют метиленхлоридом, метиленхлоридную фазу экстрагируют 2 н. винной кислотой, водную фазу подщелачивают и экстрагируют метиленхлоридом..Объединенные метиленхлоридные экстракты сушат над сульфатом магни , растворитель удал ют и к масл нистому остатку добавл ют эквивалентное количество малеиновой кислоты в этаноле . Получают гидромалеинат (3aRS, 4SR, 7aRS)-4-г (3 ,4-дихлорфенил)-гексагидро-4-индолинола , т.пл. 190- , Аналогичным образом получают целевые соединени , перечисленные в таблице .changing the corresponding c6, p-epoxide as an alkylating agent and carrying out the reaction at (-10) -100 ° C. Obtain the MoiVx target compounds c in the free state as base or as acid addition salts. Acid addition salts can be obtained from the free bases in a known manner, in particular, hydro-Leinate or hydromalonate and vice versa. Example. (3aRS 4SR, 7aRS) -4- (3, 4-Dichlorfenyl) -hexahydro-1- (2-hydroxyethyl) -4-indolinol. 3.8 g (3aRS, 4SR, 7aRS) -4- (3,4-dichlorophenyl) -hexahydro-4-indolinol 1.6 g of 2-bromoethanol and 4 g of sodium carbonate are heated in 50 ml of dimethyl form amide for 4 hours to 100 ° C. The resulting suspension is evaporated, the residue is treated with methylene chloride and 2, and tartaric acid. The aqueous phase is basified and the methylene chloride is extracted. The methylene chloride phase is separated, dried over sodium sulfate, evaporated and an equivalent amount of malonic acid is added to the oily residue. The hydromalonate is crystallized from ethyl acetate-ethanol, mp. . The starting material is prepared as follows. 3,4-Dichlorophenylmagnesium bromide (obtained from 4.2 g of magnesium and 38.5 g of 1-bromo-3, 4-dichlorobenzene) process 26.4 g of cis-perhydro14-4-oxo-1-indolin-carboxylic acid ethyl ester in 300 ml of tetrahydrofuran Mix for 4 hours at room temperature, mix with 100 ml of 2N. hydrochloric acid, lots and 200. ml of ether. The organic phase is washed with water, dried over sodium sulfate, the ether is removed and (3aRS, 4SR, 7aRS) -4- (3,4-dichlorophenyl) -hexahydro-4-hydroxy-1-indolin-carboxylic acid ethyl ester is obtained as an oily product. which is directly subjected to further processing. 24.9 g of the synthesized ester was dissolved in 240 ml of methanol, and 240 ml of Yun was added. caustic soda and stirred for 15 hours at boiling point. After cooling, it is extracted with methylene chloride, the methylene chloride phase is extracted with 2N. the aqueous phase is basified and extracted with methylene chloride ... The combined methylene chloride extracts are dried over magnesium sulfate, the solvent is removed and an equivalent amount of maleic acid in ethanol is added to the oily residue. A hydromaleic (3aRS, 4SR, 7aRS) -4-g (3, 4-dichlorophenyl) -hexahydro-4-indolinol hydromelinate is obtained, m.p. 190-, The target compounds listed in the table are prepared in a similar manner.
Гидромалонат Свободное основание сн,-сн 2,з-сн сн- :н снТо же 2 Ь Ь Гидромалонат Гидромасн2-сн , з,4-сн сн- :н снл еинат З-СРд 2, ,4-СН СН-СН СН140-142 113-115 178 (разл,) 134-135 196-197Gidromonat The free base of sn, -sn 2, h-sn bn-: nn Same 2 b b Hydromalonate Gidromash2-nn, g, 4-nn sn-: n unsol 3-СРд 2, 4-СН СН-СН140 -142 113-115 178 (dec) 134-135 196-197
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH575376 | 1976-05-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU656511A3 true SU656511A3 (en) | 1979-04-05 |
Family
ID=4298765
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU772472892A SU656511A3 (en) | 1976-05-07 | 1977-04-27 | Method of obtaining derivatives of hexahydro-4-indolinole and salts thereof |
Country Status (15)
| Country | Link |
|---|---|
| JP (1) | JPS52136169A (en) |
| AU (1) | AU2498177A (en) |
| BE (1) | BE854323A (en) |
| DE (1) | DE2718369A1 (en) |
| DK (1) | DK186277A (en) |
| FI (1) | FI771357A (en) |
| FR (1) | FR2364897A1 (en) |
| GB (1) | GB1575852A (en) |
| IL (1) | IL52017A0 (en) |
| NL (1) | NL7704839A (en) |
| NZ (1) | NZ184025A (en) |
| PT (1) | PT66521B (en) |
| SE (1) | SE7704879L (en) |
| SU (1) | SU656511A3 (en) |
| ZA (1) | ZA772733B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2741009A1 (en) | 1976-09-22 | 1978-03-23 | Sandoz Ag | 4-STYRYL-4-INDOLINOL DERIVATIVES, THEIR USE AND PRODUCTION |
-
1977
- 1977-04-25 DE DE19772718369 patent/DE2718369A1/en active Pending
- 1977-04-27 SU SU772472892A patent/SU656511A3/en active
- 1977-04-27 GB GB17571/77A patent/GB1575852A/en not_active Expired
- 1977-04-28 FI FI771357A patent/FI771357A/fi not_active Application Discontinuation
- 1977-04-28 DK DK186277A patent/DK186277A/en unknown
- 1977-04-28 SE SE7704879A patent/SE7704879L/en unknown
- 1977-05-03 NL NL7704839A patent/NL7704839A/en not_active Application Discontinuation
- 1977-05-05 NZ NZ184025A patent/NZ184025A/en unknown
- 1977-05-05 IL IL52017A patent/IL52017A0/en unknown
- 1977-05-05 BE BE177327A patent/BE854323A/en unknown
- 1977-05-05 PT PT66521A patent/PT66521B/en unknown
- 1977-05-06 FR FR7713808A patent/FR2364897A1/en not_active Withdrawn
- 1977-05-06 ZA ZA00772733A patent/ZA772733B/en unknown
- 1977-05-06 JP JP5131977A patent/JPS52136169A/en active Pending
- 1977-05-06 AU AU24981/77A patent/AU2498177A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| AU2498177A (en) | 1978-11-09 |
| SE7704879L (en) | 1977-11-08 |
| PT66521B (en) | 1979-01-22 |
| NZ184025A (en) | 1980-02-21 |
| DE2718369A1 (en) | 1977-11-17 |
| NL7704839A (en) | 1977-11-09 |
| JPS52136169A (en) | 1977-11-14 |
| ZA772733B (en) | 1978-12-27 |
| IL52017A0 (en) | 1977-07-31 |
| PT66521A (en) | 1977-06-01 |
| DK186277A (en) | 1977-11-08 |
| FI771357A (en) | 1977-11-08 |
| FR2364897A1 (en) | 1978-04-14 |
| GB1575852A (en) | 1980-10-01 |
| BE854323A (en) | 1977-11-07 |
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