CH204708A - Process for the preparation of an amino alcohol. - Google Patents
Process for the preparation of an amino alcohol.Info
- Publication number
- CH204708A CH204708A CH204708DA CH204708A CH 204708 A CH204708 A CH 204708A CH 204708D A CH204708D A CH 204708DA CH 204708 A CH204708 A CH 204708A
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- preparation
- alcohol
- amino
- amino alcohol
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 6
- 150000001414 amino alcohols Chemical class 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 238000003776 cleavage reaction Methods 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 230000007017 scission Effects 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- RXXVCPJUINTBRS-UHFFFAOYSA-N 2-[benzyl(methyl)amino]propan-1-ol Chemical compound OCC(C)N(C)CC1=CC=CC=C1 RXXVCPJUINTBRS-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 101700012268 Holin Proteins 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 101710124413 Portal protein Proteins 0.000 description 1
- 101710112672 Probable tape measure protein Proteins 0.000 description 1
- 101710194975 Uncharacterized protein gp14 Proteins 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000010446 mirabilite Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- RSIJVJUOQBWMIM-UHFFFAOYSA-L sodium sulfate decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[O-]S([O-])(=O)=O RSIJVJUOQBWMIM-UHFFFAOYSA-L 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 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
- C07C215/04—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 saturated
- C07C215/06—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 saturated and acyclic
- C07C215/08—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 saturated and acyclic with only one hydroxy group and one amino group bound to the carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung eines Aminoalkohols. Das vorliegende Patent betrifft ein Ver fahren zur Darstellung eines Aminealkohols und ist dadurch :gekennzeichnet, @dass man N - Methyl -benzyl-a-aminopropionsäureäthyl- ester in Gegenwart eines Lösungsmittels reduziert.
Das so erhaltene d,l-N-Methylbenzylala- ninol besitzt,die Formel
EMI0001.0016
Es ist ein farbloses 01 vom gp14 = 138 bis 140 . Es ist leicht löslich in Alkohol, Äther, Benzol, dagegen schwer löslich in Wasser.
Die neue Verbindung soll nach Trennung in die optisch aktiven Komponenten und Ab spaltung der Benzylgruppe zur Darstellung von optisch aktiven Aminoalkoholen dienen. <I>Beispiel:</I> 110,5 .g (0,5 Mol) N-Methyl-benzyl-a- aminopropionsäureäthylester:
EMI0001.0027
werden in 1 Liter mit,'iWg-butylat entwässer- tem Butylalkohol gelöst und die Lösung zum Sieden erhitzt.
Nun werden in die siedende Lösung 100 .g zerschnittenes Natrium mög lichst rasch eingetragen. Darauf wird unter Zusatz einer weiteren Menge entwässertem Butylalkohol weiter erhitzt, bis alles Metall gelöst ist. Man lässt abkühlen, versetzt mit 2-00 g Fis und neutralisiert mit verd. Salz säure (2 : 1) unter guter Aussenkühlung.
Man filtriert vom ausgeschiedenen Salz ab und destilliert den Alkohol im Vakuum voll6tän- dig ab. Der erhaltene Rückstand wird mit überschüssiger Natronlauge versetzt und das in Formeines Öls ausgeschiedene rohe d,l-N- Methyl-benzylalaninol in Äher aufgenom men.
Die Lösung wird mit Glaubersalz ge trocknet. Nach dem Abdestillieren des Athers hinterbleibt ein gefärbter .Sirup, der im Va kuum fraktioniert wird.
EMI0002.0001
Das <SEP> d,1-N-1VIethyl-benzy <SEP> 1-alaniirol <SEP> besitzt
<tb> die <SEP> Formel
EMI0002.0002
Farbloses<B>01</B> vom Kp" = 13,8 bis 140 . Leicht löslich in Alkohol, Äther, Benzol. Schwer löslieli in Wasser.
EMI0002.0007
5,263 <SEP> mg <SEP> Substanz <SEP> gaben <SEP> 0,355 <SEP> ein" <SEP> hT, <SEP> <B>(</B>19 <SEP> , <SEP> <B>749</B> <SEP> mm).
<tb> 0,2893 <SEP> g <SEP> Substanz <SEP> verbrauchten <SEP> 15,76 <SEP> ein' <SEP> n/10 <SEP> HCl <SEP> (= <SEP> 0,0574 <SEP> g <SEP> HCl).
<tb> C"H,-;ON <SEP> Ber. <SEP> N <SEP> = <SEP> 7,82 <SEP> % <SEP> Mol.=Cew. <SEP> = <SEP> 179.
<tb> Gef. <SEP> N <SEP> = <SEP> <B>7377</B> <SEP> % <SEP> gol.-Czew. <SEP> =183,6.
Process for the preparation of an amino alcohol. The present patent relates to a process for the preparation of an amine alcohol and is characterized in that: @that one reduces N - methylbenzyl-a-aminopropionic acid ethyl ester in the presence of a solvent.
The d, l-N-methylbenzylalaninol thus obtained has the formula
EMI0001.0016
It is a colorless 01 from gp14 = 138 to 140. It is easily soluble in alcohol, ether and benzene, on the other hand it is sparingly soluble in water.
After separation into the optically active components and cleavage of the benzyl group, the new compound is intended to be used for the preparation of optically active amino alcohols. <I> Example: </I> 110.5 g (0.5 mol) N-methyl-benzyl-a-aminopropionic acid ethyl ester:
EMI0001.0027
are dissolved in 1 liter of butyl alcohol dehydrated with "iWg-butylat" and the solution is heated to the boil.
Now 100 g of cut sodium are added as quickly as possible to the boiling solution. Then, with the addition of a further amount of dehydrated butyl alcohol, heating is continued until all of the metal has dissolved. It is allowed to cool, 2-00 g of Fis are added and the mixture is neutralized with dilute hydrochloric acid (2: 1) with good external cooling.
The precipitated salt is filtered off and the alcohol is completely distilled off in vacuo. The residue obtained is mixed with excess sodium hydroxide solution and the crude d, l-N-methylbenzylalaninol which has separated out in the form of an oil is taken up in ether.
The solution is dried with Glauber's salt. After the ether has been distilled off, a colored syrup remains, which is fractionated in a vacuum.
EMI0002.0001
The <SEP> d, 1-N-1VIethyl-benzy <SEP> 1-alaniirole <SEP> has
<tb> the <SEP> formula
EMI0002.0002
Colorless <B> 01 </B> with bp "= 13.8 to 140. Easily soluble in alcohol, ether, benzene. Slightly soluble in water.
EMI0002.0007
5.263 <SEP> mg <SEP> substance <SEP> entered <SEP> 0.355 <SEP> "<SEP> hT, <SEP> <B> (</B> 19 <SEP>, <SEP> <B> 749 </B> <SEP> mm).
<tb> 0.2893 <SEP> g <SEP> substance <SEP> consumed <SEP> 15.76 <SEP> a '<SEP> n / 10 <SEP> HCl <SEP> (= <SEP> 0.0574 <SEP> g <SEP> HCl).
<tb> C "H, -; ON <SEP> Ber. <SEP> N <SEP> = <SEP> 7.82 <SEP>% <SEP> Mol. = Cew. <SEP> = <SEP> 179.
<tb> Found <SEP> N <SEP> = <SEP> <B> 7377 </B> <SEP>% <SEP> gol.-Czew. <SEP> = 183.6.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH204708T | 1937-07-21 | ||
| CH200996T | 1938-11-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH204708A true CH204708A (en) | 1939-05-15 |
Family
ID=25723621
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH204708D CH204708A (en) | 1937-07-21 | 1937-07-21 | Process for the preparation of an amino alcohol. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH204708A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2573605A (en) * | 1946-12-02 | 1951-10-30 | Parke Davis & Co | Tertiary amines and methods for obtaining the same |
| US2573606A (en) * | 1946-12-02 | 1951-10-30 | Parke Davis & Co | Lower alkyl and alkenyl n-(1-naphthyl methyl) n-hydroxyethyl amines |
| FR2618148A1 (en) * | 1987-07-16 | 1989-01-20 | Adir | NOVEL PROCESS FOR THE ENANTIOSPECIFIC PREPARATION OF (S) ETHYLAMINO-2 (TRIFLUOROMETHYL-3-PHENYL) -1 PROPANE |
-
1937
- 1937-07-21 CH CH204708D patent/CH204708A/en unknown
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2573605A (en) * | 1946-12-02 | 1951-10-30 | Parke Davis & Co | Tertiary amines and methods for obtaining the same |
| US2573606A (en) * | 1946-12-02 | 1951-10-30 | Parke Davis & Co | Lower alkyl and alkenyl n-(1-naphthyl methyl) n-hydroxyethyl amines |
| FR2618148A1 (en) * | 1987-07-16 | 1989-01-20 | Adir | NOVEL PROCESS FOR THE ENANTIOSPECIFIC PREPARATION OF (S) ETHYLAMINO-2 (TRIFLUOROMETHYL-3-PHENYL) -1 PROPANE |
| EP0301925A1 (en) * | 1987-07-16 | 1989-02-01 | Adir Et Compagnie | Process for the enantiospecific preparation of (S)2-ethyl amino-1-3-(trifluoromethyl phenyl) propane |
| GR880100293A (en) * | 1987-07-16 | 1989-04-12 | Adir | Novel preparation process of enantiospecific (visually active) s ethylamino-2(trifluoromethyl-3phenyl)-1propane |
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