CH138199A - Process for N-alkylation with an aminoalkyl halide. - Google Patents
Process for N-alkylation with an aminoalkyl halide.Info
- Publication number
- CH138199A CH138199A CH138199DA CH138199A CH 138199 A CH138199 A CH 138199A CH 138199D A CH138199D A CH 138199DA CH 138199 A CH138199 A CH 138199A
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- alkylation
- aminoalkyl halide
- base
- halide
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 3
- 238000007126 N-alkylation reaction Methods 0.000 title description 2
- -1 aminoalkyl halide Chemical class 0.000 title 1
- IMPPGHMHELILKG-UHFFFAOYSA-N 4-ethoxyaniline Chemical compound CCOC1=CC=C(N)C=C1 IMPPGHMHELILKG-UHFFFAOYSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 239000013067 intermediate product Substances 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000012230 colorless oil Substances 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 229940072033 potash Drugs 0.000 description 2
- 235000015320 potassium carbonate Nutrition 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000001035 drying Methods 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur N-Alkylier ung mit einem Aminoalhylhalogenid. Vorliegende Erfindung bezieht sich auf die Darstellung einer monoalkylierten Base von der Formel:
EMI0001.0006
die als Pharmazeutikum und als Zwischen produkt zu solchem verwendet werden kann. Die Herstellung geschieht derart, dass man p-Phenetidin auf halogenwasserstoffsaures a- Dimethylamino-fl-methyl-y-chlorbutan ein wirken lässt und die durch Alkalien frei gemachte Base reinigt.
Die freie Base ist ein farbloses 01 vom Siedepunkt 162-164 C unter 5 mm Druck. Beispiel: 274 Gewichtsteile p-Phenetidin werden mit<B>186</B> Gewichtsteilen chlorwasserstoff- saurem a-Dimethylamino-ss-methyl-y-chlor- butan zwölf Stunden bei 120-130'C ver schmolzen. Die Schmelze wird in Wasser aufgenommen, mit Pottasche alkalisch ge macht und die freie Base in wenig Äther oder Benzol gelöst.
Nach Trocknen über Pottasche wird zur Trennung von überschüs sigem p-Phenetidin fraktioniert destilliert und dabei die monoalkylierte Base als farb loses 01 vom Siedepunkt 162-164'C .unter 5 mm Druck erhalten.
Process for N-alkylation with an aminoalhyl halide. The present invention relates to the preparation of a monoalkylated base of the formula:
EMI0001.0006
which can be used as a pharmaceutical and as an intermediate to such. The production takes place in such a way that p-phenetidine is allowed to act on a-dimethylamino-fl-methyl-y-chlorobutane which is hydrogen halide and the base liberated by alkalis is purified.
The free base is a colorless oil with a boiling point of 162-164 C under 5 mm pressure. Example: 274 parts by weight of p-phenetidine are melted with <B> 186 </B> parts by weight of a-dimethylamino-ss-methyl-y-chlorobutane for twelve hours at 120-130 ° C. The melt is taken up in water, made alkaline with potash and the free base is dissolved in a little ether or benzene.
After drying over potash, the excess p-phenetidine is separated by fractional distillation and the monoalkylated base is obtained as colorless oil with a boiling point of 162-164 ° C. under 5 mm pressure.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE138199X | 1927-01-25 | ||
| CH134094T | 1928-01-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH138199A true CH138199A (en) | 1930-02-15 |
Family
ID=25712226
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH138199D CH138199A (en) | 1927-01-25 | 1928-01-12 | Process for N-alkylation with an aminoalkyl halide. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH138199A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2687414A (en) * | 1948-11-26 | 1954-08-24 | Searle & Co | Method for producing aromatic aminoalkyl amines |
-
1928
- 1928-01-12 CH CH138199D patent/CH138199A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2687414A (en) * | 1948-11-26 | 1954-08-24 | Searle & Co | Method for producing aromatic aminoalkyl amines |
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