SU516343A3 - Method for producing isopropylamines - Google Patents
Method for producing isopropylaminesInfo
- Publication number
- SU516343A3 SU516343A3 SU1919491A SU1919491A SU516343A3 SU 516343 A3 SU516343 A3 SU 516343A3 SU 1919491 A SU1919491 A SU 1919491A SU 1919491 A SU1919491 A SU 1919491A SU 516343 A3 SU516343 A3 SU 516343A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- isopropylamines
- producing
- propanol
- amino
- preparation
- Prior art date
Links
Classifications
-
- 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
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
Изобретение относитс к новому способу получени изопропиламинов общей формулыThe invention relates to a new process for the preparation of isopropylamines of the general formula
БгО-СНг-СН- СН2-Ж-С11 BgO-SNg-CH-CH2-W-C11
СН. ОНCH. HE
или их солей,or their salts,
где RI - толильпа или нафтильна группа, обладающих терапевтической активностью.where RI is a tolilpa or naphthyl group with therapeutic activity.
Известен способ получени изопропиламинов взаимодействием 1-хлор-З-арилоксипропанола-2 с изопропиламином, а также фенола с 1-хлор-З-изопропиламинопропанолом-2 . Однако выход целевых продуктов по этому способу не превышает 30%.A known method for producing isopropylamines by reacting 1-chloro-3-aryloxypropanol-2 with isopropylamine, as well as phenol with 1-chloro-3-isopropylaminopropanol-2. However, the yield of the target products by this method does not exceed 30%.
Предлагаемый за вител ми способ получени изопропиламинов позвол ет получать более чистые целевые продукты с большим выходом - до 80%. Способ заключаетс в том, что первичный амин общей формулыA proposed method for the preparation of isopropylamines allows to obtain cleaner target products with a high yield of up to 80%. The method is that the primary amine of the general formula
R О - GH - CHs - NHa,R O - GH - CHs - NHa,
ОНHE
где RI - толильна или нафтильна группа, ввод т в реакцию с ароматическим альдегидом RS-СНО, где R2 - фенильна группа, замещенна одной или несколькими метоксиили этоксигруппами, метилендиоксигруппой или нитрогруппой. Полученное при этом основание Шиффа подвергают каталитическомуwhere RI is a tolyl or naphthyl group, is reacted with an aromatic aldehyde RS-CHO, where R2 is a phenyl group substituted by one or more methoxy or ethoxy groups, methylenedioxy group or nitro group. The resulting Schiff base is subjected to a catalytic
гидрированию в присутствии ацетона с выделением целевого продукта известным способом .hydrogenation in the presence of acetone with the selection of the target product in a known manner.
Исходные первичные амины могут быть получены известными способами при взаимодействии 3-арилокси-2,3-эпоксипропана с аммиаком .The original primary amines can be obtained by known methods by reacting 3-aryloxy-2,3-epoxypropane with ammonia.
Пример. Получение 1-(4-метоксибензаль ) -амино-3- (а-нафтокси) -пропанола-2.Example. Preparation of 1- (4-methoxybenzal) -amino-3- (a-naphthoxy) -propanol-2.
Раствор ют 21,7 г (0,1 моль) 1-амино-3-(анафтокси )-пропанола-2 в 250 мл сухого бензола и прибавл ют 15 г анисового альдегида. Кип т т реакционную смесь и удал ют воду азеотропной дистилл цией. После удалени всей воды из системы, гор чую смесь21.7 g (0.1 mol) of 1-amino-3- (anaptoxy) propanol-2 is dissolved in 250 ml of dry benzene and 15 g of anisic aldehyde are added. The reaction mixture is boiled and the water is removed by azeotropic distillation. After removing all the water from the system, the hot mixture
обрабатывают активированным углем дл обесцвечивани , фильтруют и упаривают фильтрат. Отфильтровывают выпавшие кристаллы и промывают их эфиром. Получают 30,5 г (91%) 1-(метоксибензаль)-амино-З (а-нафтокси)-пропанол-2; с т. пл. 99-103°С (после перекристаллизации из изопропанола). Вычислено дл CsiHsiNOa, %: С 75,20; Н 6,31; N 4,18. Найдено, %: С 75,62; Н 6,39; N 4,23.treated with activated carbon for decolorization; filtered; and the filtrate was evaporated. The precipitated crystals are filtered off and washed with ether. 30.5 g (91%) of 1- (methoxybenzal) -amino-3 (a-naphthoxy) -propanol-2 are obtained; with t. pl. 99-103 ° C (after recrystallization from isopropanol). Calculated for CsiHsiNOa,%: C, 75.20; H 6.31; N 4.18. Found,%: C 75.62; H 6.39; N 4.23.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HUEE002079 HU167262B (en) | 1972-12-22 | 1972-12-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU516343A3 true SU516343A3 (en) | 1976-05-30 |
Family
ID=10995469
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1919491A SU516343A3 (en) | 1972-12-22 | 1973-04-30 | Method for producing isopropylamines |
Country Status (13)
| Country | Link |
|---|---|
| JP (1) | JPS523928B2 (en) |
| AT (1) | AT320626B (en) |
| CA (1) | CA989868A (en) |
| CH (1) | CH578506A5 (en) |
| CS (1) | CS166840B2 (en) |
| DD (1) | DD106162A5 (en) |
| DE (1) | DE2322053A1 (en) |
| ES (1) | ES414204A1 (en) |
| FI (1) | FI55176C (en) |
| HU (1) | HU167262B (en) |
| SE (1) | SE395270B (en) |
| SU (1) | SU516343A3 (en) |
| YU (1) | YU36149B (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS52125940U (en) * | 1976-03-22 | 1977-09-24 | ||
| US4294966A (en) * | 1978-07-28 | 1981-10-13 | Ciba-Geigy Corporation | Process for inverting the configuration in optically active compounds |
| DE3544172A1 (en) * | 1985-12-13 | 1987-06-19 | Lentia Gmbh | NEW CRYSTALLINE SALTS OF ARYLOXY PROPANOLAMINES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE |
| IT1317817B1 (en) * | 2000-02-08 | 2003-07-15 | Bracco Spa | PROCESS FOR THE PURIFICATION OF 3-AMINO-1,2-PROPANDIOL E2-AMINO-1,3-PROPANDIOL, IN PARTICULAR IN THE SUMMARY OF MEANS OF |
| CN116178185A (en) * | 2018-04-20 | 2023-05-30 | 北京睿创康泰医药研究院有限公司 | New crystalline forms of propranolol free base |
-
1972
- 1972-12-22 HU HUEE002079 patent/HU167262B/hu not_active IP Right Cessation
-
1973
- 1973-04-06 CH CH500373A patent/CH578506A5/xx not_active IP Right Cessation
- 1973-04-11 YU YU98273A patent/YU36149B/en unknown
- 1973-04-12 FI FI116673A patent/FI55176C/en active
- 1973-04-16 AT AT336873A patent/AT320626B/en not_active IP Right Cessation
- 1973-04-17 SE SE7305484A patent/SE395270B/en unknown
- 1973-04-23 DD DD17033173A patent/DD106162A5/xx unknown
- 1973-04-24 CA CA169,415A patent/CA989868A/en not_active Expired
- 1973-04-24 CS CS293073A patent/CS166840B2/cs unknown
- 1973-04-28 ES ES414204A patent/ES414204A1/en not_active Expired
- 1973-04-30 SU SU1919491A patent/SU516343A3/en active
- 1973-05-02 DE DE19732322053 patent/DE2322053A1/en active Pending
- 1973-07-18 JP JP8040673A patent/JPS523928B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| AT320626B (en) | 1975-02-25 |
| SE395270B (en) | 1977-08-08 |
| DD106162A5 (en) | 1974-06-05 |
| JPS523928B2 (en) | 1977-01-31 |
| FI55176C (en) | 1979-06-11 |
| YU98273A (en) | 1981-06-30 |
| JPS5018427A (en) | 1975-02-26 |
| YU36149B (en) | 1982-02-25 |
| FI55176B (en) | 1979-02-28 |
| CH578506A5 (en) | 1976-08-13 |
| ES414204A1 (en) | 1976-01-16 |
| CA989868A (en) | 1976-05-25 |
| DE2322053A1 (en) | 1974-07-11 |
| HU167262B (en) | 1975-09-27 |
| CS166840B2 (en) | 1976-03-29 |
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