DE3408850A1 - Verfahren zur herstellung von threo-1-phenyl-2-amino-propanolen-(1) - Google Patents
Verfahren zur herstellung von threo-1-phenyl-2-amino-propanolen-(1)Info
- Publication number
- DE3408850A1 DE3408850A1 DE19843408850 DE3408850A DE3408850A1 DE 3408850 A1 DE3408850 A1 DE 3408850A1 DE 19843408850 DE19843408850 DE 19843408850 DE 3408850 A DE3408850 A DE 3408850A DE 3408850 A1 DE3408850 A1 DE 3408850A1
- Authority
- DE
- Germany
- Prior art keywords
- threo
- phenyl
- preparation
- aminopropan
- ols
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 title claims abstract description 13
- 238000002360 preparation method Methods 0.000 title claims abstract description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims abstract description 30
- 239000002253 acid Substances 0.000 claims abstract description 9
- 229910052500 inorganic mineral Inorganic materials 0.000 claims abstract description 8
- 239000011707 mineral Substances 0.000 claims abstract description 8
- 239000000047 product Substances 0.000 claims abstract description 7
- 230000021736 acetylation Effects 0.000 claims abstract description 6
- 238000006640 acetylation reaction Methods 0.000 claims abstract description 6
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 5
- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical class O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 claims abstract description 4
- 238000007127 saponification reaction Methods 0.000 claims description 4
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
- DLNKOYKMWOXYQA-UHFFFAOYSA-N dl-pseudophenylpropanolamine Natural products CC(N)C(O)C1=CC=CC=C1 DLNKOYKMWOXYQA-UHFFFAOYSA-N 0.000 description 13
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical group S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- DLNKOYKMWOXYQA-CBAPKCEASA-N (-)-norephedrine Chemical compound C[C@H](N)[C@H](O)C1=CC=CC=C1 DLNKOYKMWOXYQA-CBAPKCEASA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 229960003609 cathine Drugs 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- -1 amino- Chemical class 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- DLNKOYKMWOXYQA-IONNQARKSA-N cathine Chemical compound C[C@H](N)[C@@H](O)C1=CC=CC=C1 DLNKOYKMWOXYQA-IONNQARKSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- DLNKOYKMWOXYQA-VXNVDRBHSA-N (+)-norephedrine Chemical compound C[C@@H](N)[C@@H](O)C1=CC=CC=C1 DLNKOYKMWOXYQA-VXNVDRBHSA-N 0.000 description 2
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical class C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001414 amino alcohols Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 150000003840 hydrochlorides Chemical class 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- DLNKOYKMWOXYQA-APPZFPTMSA-N phenylpropanolamine Chemical compound C[C@@H](N)[C@H](O)C1=CC=CC=C1 DLNKOYKMWOXYQA-APPZFPTMSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- JYMAASGIKPNKOV-UHFFFAOYSA-N 1-chloro-1-phenylpropan-2-amine Chemical compound CC(N)C(Cl)C1=CC=CC=C1 JYMAASGIKPNKOV-UHFFFAOYSA-N 0.000 description 1
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical group CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 description 1
- 125000003047 N-acetyl group Chemical group 0.000 description 1
- 230000000397 acetylating effect Effects 0.000 description 1
- 230000003113 alkalizing effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 150000002917 oxazolidines Chemical class 0.000 description 1
- 229960000395 phenylpropanolamine Drugs 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical class CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000006462 rearrangement reaction Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C215/22—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated
- C07C215/28—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated and containing six-membered aromatic rings
- C07C215/30—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated and containing six-membered aromatic rings containing hydroxy groups and carbon atoms of six-membered aromatic rings bound to the same carbon atom of the carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19843408850 DE3408850A1 (de) | 1983-03-12 | 1984-03-10 | Verfahren zur herstellung von threo-1-phenyl-2-amino-propanolen-(1) |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3308924 | 1983-03-12 | ||
| DE19843408850 DE3408850A1 (de) | 1983-03-12 | 1984-03-10 | Verfahren zur herstellung von threo-1-phenyl-2-amino-propanolen-(1) |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3408850A1 true DE3408850A1 (de) | 1984-09-13 |
| DE3408850C2 DE3408850C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1989-03-30 |
Family
ID=25809001
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19843408850 Granted DE3408850A1 (de) | 1983-03-12 | 1984-03-10 | Verfahren zur herstellung von threo-1-phenyl-2-amino-propanolen-(1) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE3408850A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2057113A4 (en) * | 2006-08-29 | 2014-04-09 | Univ Illinois State | METHOD FOR PRODUCING PSEUDONOREPHEDRINE |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102017210944B4 (de) | 2017-06-28 | 2019-05-23 | Technische Universität Dresden | Alkoholdehydrogenasen und Verfahren zur stereoselektiven Reduktion von Carbonylverbindungen |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3230333A1 (de) * | 1982-01-13 | 1983-07-21 | Knoll Ag, 6700 Ludwigshafen | Verfahren zur herstellung von threo-1-phenyl-2-amino-propanol-(1)-derivaten |
-
1984
- 1984-03-10 DE DE19843408850 patent/DE3408850A1/de active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3230333A1 (de) * | 1982-01-13 | 1983-07-21 | Knoll Ag, 6700 Ludwigshafen | Verfahren zur herstellung von threo-1-phenyl-2-amino-propanol-(1)-derivaten |
Non-Patent Citations (1)
| Title |
|---|
| Arch. Pharm. 288, 1955, 563-582 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2057113A4 (en) * | 2006-08-29 | 2014-04-09 | Univ Illinois State | METHOD FOR PRODUCING PSEUDONOREPHEDRINE |
Also Published As
| Publication number | Publication date |
|---|---|
| DE3408850C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1989-03-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition |