SU285645A1 - METHOD OF OBTAINING 1- - Google Patents
METHOD OF OBTAINING 1-Info
- Publication number
- SU285645A1 SU285645A1 SU1160571A SU1160571A SU285645A1 SU 285645 A1 SU285645 A1 SU 285645A1 SU 1160571 A SU1160571 A SU 1160571A SU 1160571 A SU1160571 A SU 1160571A SU 285645 A1 SU285645 A1 SU 285645A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- ether
- chlorophenyl
- mercapto
- evaporated
- obtaining
- Prior art date
Links
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- KLHRXNDEAPDDME-UHFFFAOYSA-N N-[1-(4-chlorophenyl)propan-2-yl]thiohydroxylamine Chemical compound SNC(C)CC1=CC=C(Cl)C=C1 KLHRXNDEAPDDME-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 229910052987 metal hydride Inorganic materials 0.000 description 2
- 150000004681 metal hydrides Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- VIUDWXCHYJJHLD-UHFFFAOYSA-N 1-(4-chlorophenyl)sulfanylpropan-2-one Chemical compound CC(=O)CSC1=CC=C(Cl)C=C1 VIUDWXCHYJJHLD-UHFFFAOYSA-N 0.000 description 1
- XWPVILYUAOFSHM-UHFFFAOYSA-N CC(C(C1=CC=C(C=C1)Cl)S)N Chemical compound CC(C(C1=CC=C(C=C1)Cl)S)N XWPVILYUAOFSHM-UHFFFAOYSA-N 0.000 description 1
- 206010008415 Chediak-Higashi syndrome Diseases 0.000 description 1
- 230000002378 acidificating Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N iso-propanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L na2so4 Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- YOQDYZUWIQVZSF-UHFFFAOYSA-N sodium borohydride Substances [BH4-].[Na+] YOQDYZUWIQVZSF-UHFFFAOYSA-N 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- ODGROJYWQXFQOZ-UHFFFAOYSA-N sodium;boron(1-) Chemical compound [B-].[Na+] ODGROJYWQXFQOZ-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
Description
Изобретение касаетс способа получени не известных ранее аминов, которые обладают физиологической активностью и могут найти применение в медицине.The invention relates to a process for the preparation of previously unknown amines, which have physiological activity and can be used in medicine.
Предлагаетс способ получени 1-(4-хлорфенил ) меркапто-2-пропиламина формулыA method is proposed for preparing 1- (4-chlorophenyl) mercapto-2-propylamine of formula
- СН,- CH-NHj СНз - CH, - CH-NHj CH3
заключающийс в том, что соединение формулыthe fact that the compound of the formula
/ Ч/ H
С1C1
-S-CHj-C-R СНз-S-CHj-C-R CHS
где R° - иминогруппа,where R ° - imino group,
восстанавливают водородом или гидридами металлов с последующим выделением целевого продукта известными способами в виде основани или соли.is reduced by hydrogen or metal hydrides, followed by isolation of the target product by known methods as a base or salt.
Рене при комнатной температуре в течение 17 час. После удалени катализатора фильтрат испар ют досуха, остаток раствор ют в эфире и эфирный раствор экстрагируют разбавленной сол ной кислотой. Кислый экстракт довод т до щелочной реакции и экстрагируют эфиром. Органический экстракт промывают, сушат и испар ют. Полученный остаток 1-(4хлорфенил )меркапто-2-пропиламина раствор ют в эфире и обрабатывают газообразным хлористым водородом в изопропаноле. Полученный гидрохлорид перекристаллизовывают из смеси метанола и эфира, т. пл. 153°С.Rene at room temperature for 17 hours. After removing the catalyst, the filtrate is evaporated to dryness, the residue is dissolved in ether and the ether solution is extracted with dilute hydrochloric acid. The acidic extract is made alkaline and extracted with ether. The organic extract is washed, dried and evaporated. The resulting residue of 1- (4 chlorophenyl) mercapto-2-propylamine is dissolved in ether and treated with gaseous hydrogen chloride in isopropanol. The resulting hydrochloride is recrystallized from a mixture of methanol and ether, so pl. 153 ° C.
П р и м е р 2. Раствор 5 г 4-хлорфенилмеркаптоацетона в 50 Л1Л насыщенного аммиаком метанола оставл ют сто ть в течение 16 час при комнатной температуре. Растворитель выпаривают при уменьшенном давлении и остаток , содержащий 1-(4-хлорфенил) меркапто-2иминопропан , раствор ют в 10 мл метанола. Прибавл ют 1 г боргидрида натри и нагревают смесь в течение 1 час с обратным холодильником . Прибавл ют воду, экстрагируютEXAMPLE 2 A solution of 5 g of 4-chlorophenylmercaptoacetone in 50 L1L of methanol saturated with ammonia is left to stand for 16 hours at room temperature. The solvent is evaporated under reduced pressure and the residue, containing 1- (4-chlorophenyl) mercapto-2-aminopropane, is dissolved in 10 ml of methanol. 1 g of sodium borohydride is added and the mixture is heated for 1 hour under reflux. Water is added, extracted
эфиром и промывают органический раствор водой, сушат над безводным сульфатом натри и выпаривают досуха. Получают 1-(4-хлорфенил ) -меркапто-2-пропиламин, гидрохлорид которого после нерекристаллизации из мета3 Поедмет изобретени Способ получени 1-(4-хлорфенил)меркапто2-пропиламина формулы Ci V CHrCH-NH, /I СН,з отличшощийс тем, что соединение формулы Ю 4 /.-v„ Cl- S-CHr-C R - R° - иминогруппа, восстанавливают водородом или гидридами металлов с последующим выделением целевого продукта известными способами в виде основани или соли.ether, and the organic solution is washed with water, dried over anhydrous sodium sulfate, and evaporated to dryness. The 1- (4-chlorophenyl) -mercapto-2-propylamine is obtained, the hydrochloride of which after non-recrystallization from meth3. Sed of the invention. that the compound of the formula U 4 / .-v "Cl-S-CHr-C R - R ° is an imino group, is reduced by hydrogen or metal hydrides followed by isolation of the target product by known methods as a base or salt.
Publications (2)
Publication Number | Publication Date |
---|---|
SU300994A1 SU300994A1 (en) | |
SU285645A1 true SU285645A1 (en) |
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