Method for the preparation of arylalkanolamineacylates
AssigneeHoechst Celanese Corporation
InventorsAhmed M. Tafesh, Olan S. Fruchey, Charles B. Hilton
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Abstract
Acylamides or amine acylate salts of arylalkanolamines are prepared by reacting an arylisonitrosoalkanone with hydrogen and a carboxylic acid, carboxylic acid anhydride or carboxylic acid ester or mixture thereof in the presence of a transition metal catalyst; optionally the product is converted to the corresponding arylalkanolamine hydrochloride salt by reaction of the acylamide or amine acylate salt of the arylalkanolamine with hydrogen chloride in a C.sub.1 -C.sub.3 alkyl alcohol.
Claims18
A method of preparing the amine acylate salt of an arylalkanolamine, which comprises the steps of:
- a) providing a compound of the formula ##STR10## wherein, R.sub.1 =an hydroxyl alkyl, or alkyloxy radical
- R.sub.2 =hydrogen or a C.sub.1 -C.sub.8 alkyl or cycloalkyl radical, and
- Ar=an unsubstituted phenyl radical, or a phenyl radical substituted at the ortho position, the para position, or both the ortho and para positions, or an unsubstituted naphthyl radical, or a naphthyl radical substituted at one or more of the 1, 3, 6, and 7 positions, wherein the substituents are selected from the group consisting of hydroxyl, alkoxy, alkyl, phenyl, and benzyl radicals, wherein the alkyl component is a branched or unbranched C.sub.1 -C.sub.8 alkyl radical, wherein any of said alkyl, phenyl, and benzyl radicals are optionally substituted with one or more substituents selected from amino, hydroxyl, sulfonic acid, and sulfinic acid radicals, and wherein said phenyl and benzyl substituents are optionally substituted with a C.sub.1 -C.sub.8 alkyl or C.sub.1 -C.sub.8 alkoxy radical, or both;
- and
- b) reacting said compound with hydrogen in a reaction medium comprising an acyl donor selected from carboxylic acids having a melting point below 100.degree. C. and a hydrogenation catalyst comprising a transition metal catalyst on an inert support, to form a carboxylic acid salt of an arylalkanolamine.
A method of producing 1-(o- or p-hydroxyphenyl)-1-ethan-1-ol-2-amine-acetate, which comprises the steps of:
- a) providing the compound o- or p-hydroxy-.alpha.-isonitrosocetophenone;
- b) reacting said compound with hydrogen in a reaction medium comprising an acyl donor selected from carboxylic acids having a melting point less than 100.degree. C. and a transition metal catalyst on an inert support.
Dependencies are inferred from the claim text.