GB607772A - Improvements in or relating to the production of 1-(3,4-dihydroxyphenyl)-2-amino-1-butanol and new intermediates thereof - Google Patents
Improvements in or relating to the production of 1-(3,4-dihydroxyphenyl)-2-amino-1-butanol and new intermediates thereofInfo
- Publication number
- GB607772A GB607772A GB9262/45A GB926245A GB607772A GB 607772 A GB607772 A GB 607772A GB 9262/45 A GB9262/45 A GB 9262/45A GB 926245 A GB926245 A GB 926245A GB 607772 A GB607772 A GB 607772A
- Authority
- GB
- United Kingdom
- Prior art keywords
- dihydroxyphenyl
- amino
- dibenzyloxybutyrophenone
- butanol
- treating
- 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)
Abstract
Aminoketones of general formula:-<FORM:0607772/IV(b)/1> or acid addition salts thereof, wherein R represents substituted or unsubstituted diaryl-methyl and R1 and R11 represent hydrogen or arylmethyl, are obtained by treating a substituted phenone of general formula:- <FORM:0607772/IV(b)/2> wherein X represents chlorine or bromine, with a primary amine of general formula R-NH2, e.g. benzhydrylamine. The resulting product or its acid addition salt is hydrogenated catalytically to obtain a -amino-(3 : 4-dihydroxyphenyl(-butyrophenone, complete hydrogenation yielding 1-(3 : 4-dihydroxyphenyl)-2-amino-1-butanol which possesses therapeutic properties. Advantageously, palladium is used as catalyst and, while benzyl groups are preferred, other protecting arylmethyl groups, e.g. p-chloro-, p-methoxy- or p-methylbenzyl may be used. Examples are given of the preparations of: (1) a -benzhydrylamino-3 : 4-dibenzyloxybutyrophenone hydrochloride by heating under reflux a -bromo-3 : 4-dibenzyloxybutyrophenone with benzhydrylamine in absolute alcohol and subsequent treatment with dilute hydrochloric acid; (2) 1-(3 : 4-dihydroxyphenyl)-2-amino-1-butanol hydrochloride by reducing the product of (1) in absolute alcohol with hydrogen in presence of palladium sponge absorption of three moles yielding a -amino-(3 : 4 - dihydroxyphenyl) - butyrophenone hydrochloride which is either further hydrogenated in aqueous solution to obtain the requisite product or converted to and isolated as the free base. a -Bromo-3 : 4-dibenzyloxybutyrophenone is obtained by treating 3 : 4-dibenzyloxybutyrophenone with bromine in presence of methylene chloride and calcium carbonate. 3 : 4-Dibenzyloxybutyrophenone is obtained by heating under reflux a mixture of 3 : 4-dihydroxybutyrophenone, benzylchloride, anhydrous potassium carbonate, sodium iodide and alcohol. 3 : 4-Dihydroxybutyrophenone is obtained by treating catechol in chlorobenzene with n-butyryl chloride in presence of anhydrous aluminium chloride.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US607772XA | 1944-03-16 | 1944-03-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB607772A true GB607772A (en) | 1948-09-06 |
Family
ID=22031683
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB9262/45A Expired GB607772A (en) | 1944-03-16 | 1945-04-13 | Improvements in or relating to the production of 1-(3,4-dihydroxyphenyl)-2-amino-1-butanol and new intermediates thereof |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB607772A (en) |
-
1945
- 1945-04-13 GB GB9262/45A patent/GB607772A/en not_active Expired
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