AT72297B - Process for the preparation of pyrrolidine derivatives. - Google Patents
Process for the preparation of pyrrolidine derivatives.Info
- Publication number
- AT72297B AT72297B AT72297DA AT72297B AT 72297 B AT72297 B AT 72297B AT 72297D A AT72297D A AT 72297DA AT 72297 B AT72297 B AT 72297B
- Authority
- AT
- Austria
- Prior art keywords
- parts
- preparation
- pyrrolidine derivatives
- benzene
- acid ester
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 5
- 150000003235 pyrrolidines Chemical class 0.000 title claims 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 2
- 150000001299 aldehydes Chemical class 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- UVEWQKMPXAHFST-UHFFFAOYSA-N n,1-diphenylmethanimine Chemical compound C=1C=CC=CC=1C=NC1=CC=CC=C1 UVEWQKMPXAHFST-UHFFFAOYSA-N 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
- -1 pyruvic acid ester Chemical class 0.000 description 4
- LCTONWCANYUPML-UHFFFAOYSA-N PYRUVIC-ACID Natural products CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 229940107700 pyruvic acid Drugs 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 2
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- CNIAJDNSBAOSSL-UHFFFAOYSA-N 4-acetyl-5-(1,3-benzodioxol-5-ylmethyl)-1-phenylpyrrolidine-2,3-dione Chemical compound CC(=O)C1C(Cc2ccc3OCOc3c2)N(C(=O)C1=O)c1ccccc1 CNIAJDNSBAOSSL-UHFFFAOYSA-N 0.000 description 1
- WREVVZMUNPAPOV-UHFFFAOYSA-N 8-aminoquinoline Chemical compound C1=CN=C2C(N)=CC=CC2=C1 WREVVZMUNPAPOV-UHFFFAOYSA-N 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 235000019640 taste Nutrition 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyrrole Compounds (AREA)
Description
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122 Teile Anisidin und 106 Teile Benzaldehyd werden in Toluol mit 158 Teilen Azetbrenztraubensäureester 24 Stunden stehen gelassen. Nach der Reinigung resultiert obige Verbindung, die aus 96%igem Alkohol umkristallisiert, bei 225 bis 2270 unter Zersetzung schmilzt.
Beispiel 5: Darstellung von 1-Phenyl-2-piperonyl-3-azetyl-4.5-di- ketopyrrolidin.
EMI2.1
92 Teile Anilin und 150 Teile Piperenal werden in Benzol mit 160 Teilen Atetbrenztraubensäureester einige Stunden gekocht ; nach der Reinigung und Umkristallisation
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bei 166"unter Zersetzung schmilzt.
Beispiel 7: Darstellung von 1-o-Tolyl-2-p-methoxyphenylazetyl- dmotopyrrolidm.
EMI2.5
158 Teile Azetylbrenztraubensäureester und 106 Teile Anisaldehyd werden in t 000 Teilen Benzol gelöst und Im Wasseratoffstrom dazu unter Umschütteln 110 Teile frisch destilliertes o-Toluidin in 100 Teilen Benzol gel 0tt. Nach dem Eintragen wird noch
EMI2.6
kotopyrrol id in.
EMI2.7
144 Teile 8-Aminochinolin und 106 Teile Benzaldehyd werden mit Benzol mit 158 Teilen Azebrenztraubensäureester versetzt und 1 Stunde gekocht. Nach der Reinigung-
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EMI3.1
5 bis 6 Stunden auf 100 bis) 100 erhitzt. Nach der Reinigung ergibt sich die Verbindung als hellbraunes Pulver, das sich bei höherer Temperatur allmählich zenetzt. Es schmeckt bitter, gibt mit Eisenchlorid rotbraune Färbung und ist in organischen Lösungsmitteln mit Ausnahme von Äther und Petrolether Wslich.
Beispiel 10 : Darstellung von 1-Phenyl-2-furfuryl-3-azetyl-4.5-di- ketopyrrolidtn.
EMI3.2
96 Teile Furfurol, 158 Teile Azetbrenztraubensäurester und 93 Teile Anilin worden in 1000 Teilen Benzol gelöst und nach mehrstündigem Stehen 2 Stunden auf dem Wassorbade gekocht. Nach der Reinigung erhält man obige Verbindung, die, aus
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aus 50%igem alkohol erhält man Kristalle, die von etwa 205 ab erweichen und bei : u 5 bis 2170 unter Zersetzung schmelzen.
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122 parts of anisidine and 106 parts of benzaldehyde are left to stand in toluene with 158 parts of pyruvic acid ester for 24 hours. Purification results in the above compound, which recrystallizes from 96% alcohol, melts at 225 to 2270 with decomposition.
Example 5: Preparation of 1-phenyl-2-piperonyl-3-acetyl-4,5-di-ketopyrrolidine.
EMI2.1
92 parts of aniline and 150 parts of piperenal are boiled for a few hours in benzene with 160 parts of pyruvic acid ester; after purification and recrystallization
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at 166 "melts with decomposition.
Example 7: Preparation of 1-o-tolyl-2-p-methoxyphenylazetyl-dmotopyrrolidm.
EMI2.5
158 parts of acetylpyruvic acid ester and 106 parts of anisaldehyde are dissolved in 1,000 parts of benzene and 110 parts of freshly distilled o-toluidine are dissolved in 100 parts of benzene in a stream of water while shaking. After entering it will still
EMI2.6
kotopyrrol id in.
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144 parts of 8-amino quinoline and 106 parts of benzaldehyde are mixed with benzene with 158 parts of azepruvic acid ester and the mixture is boiled for 1 hour. After cleaning-
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Heated to 100 to) 100 for 5 to 6 hours. After cleaning, the compound results as a light brown powder that gradually decomposes at a higher temperature. It tastes bitter, gives a reddish-brown color with ferric chloride and is soluble in organic solvents with the exception of ether and petroleum ether.
Example 10: Preparation of 1-phenyl-2-furfuryl-3-acetyl-4,5-di-ketopyrrolidtn.
EMI3.2
96 parts of furfural, 158 parts of pyruvic acid ester and 93 parts of aniline were dissolved in 1000 parts of benzene and, after standing for several hours, boiled on the water bath for 2 hours. After purification, the above compound is obtained from
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from 50% alcohol, crystals are obtained which soften from about 205 and melt at: u 5 to 2170 with decomposition.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT72297T | 1914-03-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AT72297B true AT72297B (en) | 1916-08-25 |
Family
ID=3593962
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT72297D AT72297B (en) | 1914-03-17 | 1914-03-17 | Process for the preparation of pyrrolidine derivatives. |
Country Status (1)
| Country | Link |
|---|---|
| AT (1) | AT72297B (en) |
-
1914
- 1914-03-17 AT AT72297D patent/AT72297B/en active
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