SE444677B - Forfarande for framstellning av 1-isopropylamino-3-/4-(2-metoxietyl)fenoxi/-2-propanol - Google Patents
Forfarande for framstellning av 1-isopropylamino-3-/4-(2-metoxietyl)fenoxi/-2-propanolInfo
- Publication number
- SE444677B SE444677B SE7902821A SE7902821A SE444677B SE 444677 B SE444677 B SE 444677B SE 7902821 A SE7902821 A SE 7902821A SE 7902821 A SE7902821 A SE 7902821A SE 444677 B SE444677 B SE 444677B
- Authority
- SE
- Sweden
- Prior art keywords
- propanol
- phenoxy
- isopropylamino
- acid
- trifluoroacetic acid
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 14
- KFZMGEQAYNKOFK-UHFFFAOYSA-N 2-propanol Substances CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 title claims description 6
- KHUXNRRPPZOJPT-UHFFFAOYSA-N phenoxy radical Chemical class O=C1C=C[CH]C=C1 KHUXNRRPPZOJPT-UHFFFAOYSA-N 0.000 title 1
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 28
- AFVFQIVMOAPDHO-UHFFFAOYSA-N methanesulfonic acid Substances CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 22
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 12
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 10
- 239000012279 sodium borohydride Substances 0.000 claims description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
- IUBSYMUCCVWXPE-UHFFFAOYSA-N metoprolol Chemical compound COCCC1=CC=C(OCC(O)CNC(C)C)C=C1 IUBSYMUCCVWXPE-UHFFFAOYSA-N 0.000 claims description 8
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 238000007796 conventional method Methods 0.000 claims description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 claims description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims 2
- CLTYDMIYCODWLE-UHFFFAOYSA-N 1-[4-(3-chloro-2-hydroxypropoxy)phenyl]-2-methoxyethanone Chemical compound ClCC(COC1=CC=C(C=C1)C(=O)COC)O CLTYDMIYCODWLE-UHFFFAOYSA-N 0.000 claims 1
- CYGMBGZUOIIVSF-UHFFFAOYSA-N 1-[4-[2-hydroxy-3-(propan-2-ylamino)propoxy]phenyl]-2-methoxyethanone Chemical compound COCC(=O)C1=CC=C(OCC(O)CNC(C)C)C=C1 CYGMBGZUOIIVSF-UHFFFAOYSA-N 0.000 claims 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 1
- 230000003197 catalytic effect Effects 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 11
- 239000000543 intermediate Substances 0.000 description 11
- 229940098779 methanesulfonic acid Drugs 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 229960002237 metoprolol Drugs 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- -1 methylene compound Chemical class 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- 150000008062 acetophenones Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- QWXYZCJEXYQNEI-OSZHWHEXSA-N intermediate I Chemical compound COC(=O)[C@@]1(C=O)[C@H]2CC=[N+](C\C2=C\C)CCc2c1[nH]c1ccccc21 QWXYZCJEXYQNEI-OSZHWHEXSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 229930194542 Keto Natural products 0.000 description 1
- 239000012445 acidic reagent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 150000008366 benzophenones Chemical class 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 150000005194 ethylbenzenes Chemical class 0.000 description 1
- 239000000383 hazardous chemical Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229960001300 metoprolol tartrate Drugs 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 150000003152 propanolamines Chemical class 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003458 sulfonic acid derivatives Chemical class 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- WUBVEMGCQRSBBT-UHFFFAOYSA-N tert-butyl 4-(trifluoromethylsulfonyloxy)-3,6-dihydro-2h-pyridine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(OS(=O)(=O)C(F)(F)F)=CC1 WUBVEMGCQRSBBT-UHFFFAOYSA-N 0.000 description 1
- 239000012485 toluene extract Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C217/28—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines
- C07C217/30—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines having the oxygen atom of at least one of the etherified hydroxy groups further bound to a carbon atom of a six-membered aromatic ring
- C07C217/32—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines having the oxygen atom of at least one of the etherified hydroxy groups further bound to a carbon atom of a six-membered aromatic ring the six-membered aromatic ring or condensed ring system containing that ring being further substituted
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/70—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
- C07C45/71—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form being hydroxy groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FI781001A FI59392C (fi) | 1978-04-01 | 1978-04-01 | Foerfarande foer framstaellning av terapeutiskt aktiv 1-isopropylamino-3-(4-(2-metoxietyl)fenoxi)-2-propanol samt dess syraadditionssalter |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SE7902821L SE7902821L (sv) | 1979-10-02 |
| SE444677B true SE444677B (sv) | 1986-04-28 |
Family
ID=8511594
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE7902821A SE444677B (sv) | 1978-04-01 | 1979-03-29 | Forfarande for framstellning av 1-isopropylamino-3-/4-(2-metoxietyl)fenoxi/-2-propanol |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS54145623A (enrdf_load_stackoverflow) |
| AT (1) | AT364349B (enrdf_load_stackoverflow) |
| CH (1) | CH639065A5 (enrdf_load_stackoverflow) |
| DK (1) | DK145195C (enrdf_load_stackoverflow) |
| FI (1) | FI59392C (enrdf_load_stackoverflow) |
| NL (1) | NL7902407A (enrdf_load_stackoverflow) |
| NO (1) | NO145402C (enrdf_load_stackoverflow) |
| SE (1) | SE444677B (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI59985C (fi) * | 1980-05-26 | 1982-01-08 | Farmos Oy | Foerfarande foer framstaellning av terapeutiskt aktiv 1-isopropylamino-3-(4-(2-metoxietyl)fenoxi)-2-propanol samt dess syra-additionssalter |
-
1978
- 1978-04-01 FI FI781001A patent/FI59392C/fi not_active IP Right Cessation
-
1979
- 1979-03-12 NO NO790825A patent/NO145402C/no unknown
- 1979-03-15 AT AT0196479A patent/AT364349B/de not_active IP Right Cessation
- 1979-03-28 NL NL7902407A patent/NL7902407A/xx not_active Application Discontinuation
- 1979-03-29 SE SE7902821A patent/SE444677B/sv not_active IP Right Cessation
- 1979-03-30 DK DK131079A patent/DK145195C/da not_active IP Right Cessation
- 1979-03-30 JP JP3923679A patent/JPS54145623A/ja active Granted
- 1979-03-30 CH CH301279A patent/CH639065A5/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| FI781001A7 (fi) | 1979-10-02 |
| CH639065A5 (en) | 1983-10-31 |
| NO145402C (no) | 1982-03-17 |
| AT364349B (de) | 1981-10-12 |
| FI59392B (fi) | 1981-04-30 |
| JPS6130653B2 (enrdf_load_stackoverflow) | 1986-07-15 |
| SE7902821L (sv) | 1979-10-02 |
| JPS54145623A (en) | 1979-11-14 |
| NL7902407A (nl) | 1979-10-03 |
| DK145195B (da) | 1982-10-04 |
| ATA196479A (de) | 1981-03-15 |
| NO145402B (no) | 1981-12-07 |
| DK145195C (da) | 1983-04-05 |
| DK131079A (da) | 1979-10-02 |
| NO790825L (no) | 1979-10-02 |
| FI59392C (fi) | 1982-02-02 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| HU198437B (en) | Process for producing mono- or bis-carbonyl-compounds | |
| Giordano et al. | A general, selective, and convenient procedure of homolytic formylation of heteroaromatic bases | |
| JP2009522227A (ja) | タミフルの合成におけるエポキシド中間体 | |
| JP5724119B2 (ja) | テトラヒドロピラン−４−オン及びピラン−４−オンの製法 | |
| SE444677B (sv) | Forfarande for framstellning av 1-isopropylamino-3-/4-(2-metoxietyl)fenoxi/-2-propanol | |
| JP2830210B2 (ja) | α，β―不飽和ケトン類の合成法 | |
| EP1720851B1 (en) | Process for synthesising heliotropine and its derivatives | |
| EP1167365B1 (en) | Method of producing sesamol formic acid ester and sesamol | |
| US3845076A (en) | Method of preparing aldehydes | |
| JP3795970B2 (ja) | α，β−不飽和アルデヒドの製造方法 | |
| CN112457203A (zh) | 一种2-氨基-2-甲基-1-丙醇的制备方法 | |
| TW200408635A (en) | Optically active β-aminoketones, optically active 1, 3-amino alcohols and processes for preparing them | |
| US4194053A (en) | Process for preparing esters of α-acetyl-α'-methylsuccinic acid and esters of α-methyl-α'-acetyl-α'-(5-methyl-3-oxohexyl)succinic acid | |
| JPH0273033A (ja) | ４，４―ジメチル―１―（ｐ―クロロフエニル）ペンタン―３―オンの製造方法 | |
| US4163111A (en) | 2-Cyclopentenone derivatives | |
| JPS62164656A (ja) | シアノイソホロンの製造法 | |
| JP4030623B2 (ja) | ４−アルコキシメチルシクロヘキシルメタノール類及びその製造法 | |
| SU727615A1 (ru) | Способ получени метилвинилкетона | |
| JP4294130B2 (ja) | α，β−不飽和ケトン化合物の製造方法 | |
| CN100497312C (zh) | 5,6,7,8－四氢喹啉的制备方法 | |
| EP0348549A1 (en) | Improved process for the preparation of substituted furanones | |
| EP0362309B1 (fr) | (ethylenedioxo-3,3 cyclohexyl)-4 acetophenone et derives de ce compose, procedes pour leur preparation et utilisation de ces composes | |
| JP3227020B2 (ja) | ケタール類及びその製造法 | |
| JPH0584298B2 (enrdf_load_stackoverflow) | ||
| HU206080B (en) | Process for producing cinnamic acid nitrile derivatives |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| NUG | Patent has lapsed |
Ref document number: 7902821-3 Effective date: 19911009 Format of ref document f/p: F |