DE2322053A1 - Verfahren zur herstellung von isopropylaminen - Google Patents
Verfahren zur herstellung von isopropylaminenInfo
- Publication number
- DE2322053A1 DE2322053A1 DE19732322053 DE2322053A DE2322053A1 DE 2322053 A1 DE2322053 A1 DE 2322053A1 DE 19732322053 DE19732322053 DE 19732322053 DE 2322053 A DE2322053 A DE 2322053A DE 2322053 A1 DE2322053 A1 DE 2322053A1
- Authority
- DE
- Germany
- Prior art keywords
- acetone
- formula
- general formula
- isopropylamines
- propan
- Prior art date
- Legal status (The legal status 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 status listed.)
- Pending
Links
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 title claims abstract description 24
- 150000004753 Schiff bases Chemical class 0.000 title claims abstract description 8
- 239000002262 Schiff base Substances 0.000 title claims abstract description 7
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical class CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 title claims description 12
- 238000005984 hydrogenation reaction Methods 0.000 title abstract description 3
- 238000000034 method Methods 0.000 claims abstract description 19
- -1 methylenedioxy Chemical group 0.000 claims abstract description 13
- 150000003934 aromatic aldehydes Chemical class 0.000 claims abstract description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 4
- 238000002360 preparation method Methods 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 10
- 239000002253 acid Chemical group 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 150000003141 primary amines Chemical class 0.000 claims description 4
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 2
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 abstract description 8
- 239000007858 starting material Substances 0.000 abstract description 7
- 238000006243 chemical reaction Methods 0.000 abstract description 6
- 239000012535 impurity Substances 0.000 abstract description 4
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 abstract description 4
- 206010002383 Angina Pectoris Diseases 0.000 abstract description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 2
- 230000002265 prevention Effects 0.000 abstract description 2
- 206010003119 arrhythmia Diseases 0.000 abstract 1
- 230000006793 arrhythmia Effects 0.000 abstract 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 abstract 1
- 125000003944 tolyl group Chemical group 0.000 abstract 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 21
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 238000002844 melting Methods 0.000 description 10
- 230000008018 melting Effects 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- YJGIJBMZAQZGMM-UHFFFAOYSA-N 1-naphthalen-1-yloxypropan-2-ol Chemical compound C1=CC=C2C(OCC(O)C)=CC=CC2=C1 YJGIJBMZAQZGMM-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 238000004140 cleaning Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- BGRWYRAHAFMIBJ-UHFFFAOYSA-N 1,3-di(propan-2-yl)urea Chemical compound CC(C)NC(=O)NC(C)C BGRWYRAHAFMIBJ-UHFFFAOYSA-N 0.000 description 2
- 238000010533 azeotropic distillation Methods 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
- 239000002178 crystalline material Substances 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 2
- NXQMNKUGGYNLBY-UHFFFAOYSA-N toliprolol Chemical compound CC(C)NCC(O)COC1=CC=CC(C)=C1 NXQMNKUGGYNLBY-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- NUEKYLDQIOYNLD-UHFFFAOYSA-N 1-amino-3-(3-methylphenoxy)propan-2-ol Chemical compound CC1=CC=CC(OCC(O)CN)=C1 NUEKYLDQIOYNLD-UHFFFAOYSA-N 0.000 description 1
- NLDZKMXGSNKPTM-UHFFFAOYSA-N 1-amino-3-naphthalen-2-yloxypropan-2-ol Chemical compound C1=CC=CC2=CC(OCC(O)CN)=CC=C21 NLDZKMXGSNKPTM-UHFFFAOYSA-N 0.000 description 1
- ZRBLAFWOGCBZPV-UHFFFAOYSA-N 1-chloro-3-(propan-2-ylamino)propan-2-ol Chemical compound CC(C)NCC(O)CCl ZRBLAFWOGCBZPV-UHFFFAOYSA-N 0.000 description 1
- GVDZNWFGNHAZCX-UHFFFAOYSA-N 1-phenyl-n-propan-2-ylmethanimine Chemical compound CC(C)N=CC1=CC=CC=C1 GVDZNWFGNHAZCX-UHFFFAOYSA-N 0.000 description 1
- GSLTVFIVJMCNBH-UHFFFAOYSA-N 2-isocyanatopropane Chemical compound CC(C)N=C=O GSLTVFIVJMCNBH-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- AQHHHDLHHXJYJD-UHFFFAOYSA-N propranolol Chemical compound C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-UHFFFAOYSA-N 0.000 description 1
- ZMRUPTIKESYGQW-UHFFFAOYSA-N propranolol hydrochloride Chemical compound [H+].[Cl-].C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 ZMRUPTIKESYGQW-UHFFFAOYSA-N 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 230000033764 rhythmic process Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HUEE002079 HU167262B (enrdf_load_stackoverflow) | 1972-12-22 | 1972-12-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2322053A1 true DE2322053A1 (de) | 1974-07-11 |
Family
ID=10995469
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19732322053 Pending DE2322053A1 (de) | 1972-12-22 | 1973-05-02 | Verfahren zur herstellung von isopropylaminen |
Country Status (13)
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0007605A1 (de) * | 1978-07-28 | 1980-02-06 | Ciba-Geigy Ag | Verfahren zur Umkehrung der Konfiguration in optisch aktiven Verbindungen und dazu benötigte neue optisch aktive Zwischenprodukte und deren Salze |
| EP0229947A1 (de) * | 1985-12-13 | 1987-07-29 | Rorer International (Overseas) Inc. | Neue kristalline Salze von Aryloxy-propanolaminen, Verfahren zu ihrer Herstellung und ihre Verwendung |
| WO2001058848A1 (en) * | 2000-02-08 | 2001-08-16 | Bracco Imaging S.P.A. | A process for the purification of 3-amino-1,2-propanediol and 2-amino-1,3-propanediol |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS52125940U (enrdf_load_stackoverflow) * | 1976-03-22 | 1977-09-24 | ||
| CN116178185A (zh) * | 2018-04-20 | 2023-05-30 | 北京睿创康泰医药研究院有限公司 | 普萘洛尔游离碱的新晶型 |
-
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/xx unknown
- 1973-04-12 FI FI116673A patent/FI55176C/fi active
- 1973-04-16 AT AT336873A patent/AT320626B/de not_active IP Right Cessation
- 1973-04-17 SE SE7305484A patent/SE395270B/xx 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/es not_active Expired
- 1973-04-30 SU SU1919491A patent/SU516343A3/ru active
- 1973-05-02 DE DE19732322053 patent/DE2322053A1/de active Pending
- 1973-07-18 JP JP8040673A patent/JPS523928B2/ja not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0007605A1 (de) * | 1978-07-28 | 1980-02-06 | Ciba-Geigy Ag | Verfahren zur Umkehrung der Konfiguration in optisch aktiven Verbindungen und dazu benötigte neue optisch aktive Zwischenprodukte und deren Salze |
| EP0229947A1 (de) * | 1985-12-13 | 1987-07-29 | Rorer International (Overseas) Inc. | Neue kristalline Salze von Aryloxy-propanolaminen, Verfahren zu ihrer Herstellung und ihre Verwendung |
| WO2001058848A1 (en) * | 2000-02-08 | 2001-08-16 | Bracco Imaging S.P.A. | A process for the purification of 3-amino-1,2-propanediol and 2-amino-1,3-propanediol |
Also Published As
| Publication number | Publication date |
|---|---|
| HU167262B (enrdf_load_stackoverflow) | 1975-09-27 |
| SE395270B (sv) | 1977-08-08 |
| FI55176B (fi) | 1979-02-28 |
| JPS5018427A (enrdf_load_stackoverflow) | 1975-02-26 |
| CS166840B2 (enrdf_load_stackoverflow) | 1976-03-29 |
| DD106162A5 (enrdf_load_stackoverflow) | 1974-06-05 |
| SU516343A3 (ru) | 1976-05-30 |
| CA989868A (en) | 1976-05-25 |
| CH578506A5 (enrdf_load_stackoverflow) | 1976-08-13 |
| ES414204A1 (es) | 1976-01-16 |
| FI55176C (fi) | 1979-06-11 |
| YU98273A (en) | 1981-06-30 |
| YU36149B (en) | 1982-02-25 |
| JPS523928B2 (enrdf_load_stackoverflow) | 1977-01-31 |
| AT320626B (de) | 1975-02-25 |
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