Derivatives of 1-phenoxy-3-amino-propan-2-ol and process for their production

US3969363A · kind A · utility

Assignee

• Cassella Farbwerke Mainkur Aktiengesellschaft

Inventors

• Thomas Raabe
• Otto Grawinger · Frankfurt am Main, DE
• Josef Scholtholt · Hanau, DE
• Rolf-Eberhard Nitz · Frankfurt am Main, DE
• Eckhard Schraven · Frankfurt am Main, DE

Key dates

• Filing date: Dec 10, 1974
• Grant date: Jul 13, 1976
• Expiry date: Dec 10, 1994

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D213/85
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

The present invention relates to new pharmacologically valuable derivatives of 1-phenoxy-3-amino-propan-2-ol having the formula ##EQU1## and the aldehyde condensation products and acid addition salts thereof wherein X is selected from the group consisting of ##EQU2## wherein the phenyl ring I may have attached to it up to three similar or different substituents selected from the group consisting of alkyl, alkenyl, alkinyl, cycloalkyl, cycloalkenyl, alkoxy, alkenyloxy, alkinyloxy, benzyloxy, phenyl, halogen and --NR.sub.1 R.sub.2, wherein R.sub.1 is selected from alkyl and acyl, and R.sub.2 is selected from hydrogen and alkyl and n is 1, 2 or 3; and to the production thereof by a method selected from (A) reacting 1-phenoxy-3-amino-propan-2-ol having the formula ##EQU3## with a compound having the formula Y-X, wherein X has the above defined meaning and Y is selected from halogen, --OH, --OK or --ONa; (B) reacting a compound of the formula ##EQU4## with a compound of the formula H.sub.2 N--X, wherein X has the above-defined meaning and Z is selected from ##EQU5## and ##EQU6## (C) reacting a phenol ##EQU7## with Z--CH.sub.2 --NH--X, wherein X and Z have the meaning defined above.