DE2158619B2 - Verfahren zur Herstellung von Salzen substituierter Phenyläthanolaminen - Google Patents
Verfahren zur Herstellung von Salzen substituierter PhenyläthanolaminenInfo
- Publication number
- DE2158619B2 DE2158619B2 DE19712158619 DE2158619A DE2158619B2 DE 2158619 B2 DE2158619 B2 DE 2158619B2 DE 19712158619 DE19712158619 DE 19712158619 DE 2158619 A DE2158619 A DE 2158619A DE 2158619 B2 DE2158619 B2 DE 2158619B2
- Authority
- DE
- Germany
- Prior art keywords
- substituted
- salts
- preparation
- phenylethanolamines
- alkyl
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims description 9
- 150000003839 salts Chemical class 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 4
- ULSIYEODSMZIPX-UHFFFAOYSA-N phenylethanolamine Chemical class NCC(O)C1=CC=CC=C1 ULSIYEODSMZIPX-UHFFFAOYSA-N 0.000 title description 3
- 239000002253 acid Substances 0.000 claims description 6
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 6
- 239000011707 mineral Substances 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- SZFHAHACWVROGM-UHFFFAOYSA-N 2-phenyl-1,3-oxazolidine Chemical class N1CCOC1C1=CC=CC=C1 SZFHAHACWVROGM-UHFFFAOYSA-N 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 150000008062 acetophenones Chemical class 0.000 description 3
- 239000012452 mother liquor Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- -1 C-11 azide Chemical class 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- YRNDGUSDBCARGC-UHFFFAOYSA-N 2-methoxyacetophenone Chemical class COCC(=O)C1=CC=CC=C1 YRNDGUSDBCARGC-UHFFFAOYSA-N 0.000 description 1
- WGTBUDNMXMVQRQ-UHFFFAOYSA-N 4-methyl-5-phenyl-1,3-oxazolidine Chemical compound CC1NCOC1C1=CC=CC=C1 WGTBUDNMXMVQRQ-UHFFFAOYSA-N 0.000 description 1
- NWUMFGRLYOPOGJ-UHFFFAOYSA-N Cl.CC1NCOC1C1=CC=CC=C1 Chemical compound Cl.CC1NCOC1C1=CC=CC=C1 NWUMFGRLYOPOGJ-UHFFFAOYSA-N 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- DFYRUELUNQRZTB-UHFFFAOYSA-N apocynin Chemical compound COC1=CC(C(C)=O)=CC=C1O DFYRUELUNQRZTB-UHFFFAOYSA-N 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000002917 oxazolidines Chemical class 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000004043 responsiveness Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C225/00—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones
- C07C225/02—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton
- C07C225/14—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being unsaturated
- C07C225/16—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being unsaturated and containing six-membered aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DD15448671 | 1971-04-19 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2158619A1 DE2158619A1 (de) | 1973-08-09 |
| DE2158619B2 true DE2158619B2 (de) | 1979-10-31 |
Family
ID=5483716
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712158619 Withdrawn DE2158619B2 (de) | 1971-04-19 | 1971-11-26 | Verfahren zur Herstellung von Salzen substituierter Phenyläthanolaminen |
Country Status (6)
| Country | Link |
|---|---|
| BG (1) | BG25213A3 (enExample) |
| CS (1) | CS159795B2 (enExample) |
| DE (1) | DE2158619B2 (enExample) |
| HU (1) | HU163203B (enExample) |
| SE (1) | SE366734B (enExample) |
| SU (1) | SU493957A3 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0259782A1 (de) * | 1986-09-11 | 1988-03-16 | Dr. Karl Thomae GmbH | Neue Naphtalin- und Indanderivate, diese Verbindungen enthaltende Arzneimittel und Verfahren zu deren Herstellung |
-
1971
- 1971-11-24 CS CS819171A patent/CS159795B2/cs unknown
- 1971-11-26 DE DE19712158619 patent/DE2158619B2/de not_active Withdrawn
- 1971-12-07 BG BG019184A patent/BG25213A3/xx unknown
- 1971-12-29 HU HUAO000327 patent/HU163203B/hu unknown
-
1972
- 1972-02-09 SE SE154572A patent/SE366734B/xx unknown
- 1972-03-06 SU SU1755774A patent/SU493957A3/ru active
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0259782A1 (de) * | 1986-09-11 | 1988-03-16 | Dr. Karl Thomae GmbH | Neue Naphtalin- und Indanderivate, diese Verbindungen enthaltende Arzneimittel und Verfahren zu deren Herstellung |
Also Published As
| Publication number | Publication date |
|---|---|
| HU163203B (enExample) | 1973-07-28 |
| CS159795B2 (enExample) | 1975-01-31 |
| BG25213A3 (en) | 1978-08-10 |
| DE2158619A1 (de) | 1973-08-09 |
| SU493957A3 (ru) | 1975-11-28 |
| SE366734B (enExample) | 1974-05-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8239 | Disposal/non-payment of the annual fee |