GB396551A - Manufacture of racemic compounds of the 1-hydroxyphenyl-2-aminopropanol (1) series - Google Patents
Manufacture of racemic compounds of the 1-hydroxyphenyl-2-aminopropanol (1) seriesInfo
- Publication number
- GB396551A GB396551A GB20960/32A GB2096032A GB396551A GB 396551 A GB396551 A GB 396551A GB 20960/32 A GB20960/32 A GB 20960/32A GB 2096032 A GB2096032 A GB 2096032A GB 396551 A GB396551 A GB 396551A
- Authority
- GB
- United Kingdom
- Prior art keywords
- racemic
- palladium
- nickel
- hydroxyphenyl
- group
- 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.)
- Expired
Links
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
Racemic 1-hydroxyphenyl-2-aminopropanols (1) are prepared by reducing a l-1-hydroxyphenyl-2-ketopropanol-(1) with hydrogen at a raised temperature in the presence of ammonia or a primary or secondary amine and or a precious metal or a metal of the nickel group (iron, cobalt, nickel or copper). When using an alkylamine or arylamine, the product is alkylated or arylated in the amino group, but in the case of ammonia or an aralkylamine there is obtained a product unsubstituted in the amino group, except when an aralkylamine is used in conjunction with a catalyst of the nickel group. In the latter case, the aralkylamino compound is formed and requires to be further hydrogenated in the presence of a precious metal in order to split off the aralkyl group. The reaction is preferably effected in an alcoholic solution. Examples are given of the preparation of (1) racemic m-hydroxyphenylpropanolamine by hydrogenating l-m-hydroxyphenylacetylcarbinol in the presence of benzylamine and palladium; using nickel as the catalyst, the racemic m-hydroxyphenylbenzylaminopropanol is obtained, from which the benzyl group is split off by continuing the hydrogenation in presence of palladium; (2) racemic m-hydroxyphenylaminopropanol from l-m-hydroxyphenylacetylcarbinol using ammonia and palladium; (3) racemic p-hydroxyphenylaminopropanol by hydrogenation of l-p-hydroxyphenylacetylcarbinol in the presence of benzylamine and nickel, and hydrogenating the product in presence of palladium to split off the benzyl group; (4) racemic 3 : 4-dihydroxyphenylaminopropanol from l-3 : 4 - dihydroxyphenylacetylcarbinol using benzylamine and palladium; (5) racemic 1-m-hydroxyphenyl-2-methylaminopropanol-(1) by hydrogenation of l-m-hydroxyphenylacetylcarbinol in presence of methylamine and platinum. Laevo - 3 : 4 - dihydroxyphenylacetylcarbinol is prepared by adding protocatechuic aldehyde to the fermentation product of glucose and beer yeast and extracting with ethyl acetate.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE396551X | 1931-07-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB396551A true GB396551A (en) | 1933-08-10 |
Family
ID=6397053
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB20960/32A Expired GB396551A (en) | 1931-07-25 | 1932-07-25 | Manufacture of racemic compounds of the 1-hydroxyphenyl-2-aminopropanol (1) series |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB396551A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2774789A (en) * | 1947-10-24 | 1956-12-18 | Sterling Drug Inc | 1-arterenol and its acid-addition salts and preparation thereof |
-
1932
- 1932-07-25 GB GB20960/32A patent/GB396551A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2774789A (en) * | 1947-10-24 | 1956-12-18 | Sterling Drug Inc | 1-arterenol and its acid-addition salts and preparation thereof |
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