Catalytic synthesis of N-alkylated anilines from olefins and anilines

US6222073A · kind A · utility

Assignee

• Aventis Research & Technologies GmbH & Co. · DE

Inventors

• Jurgen Herwig
• Matthias Beller · Ostseebad Nienhagen, DE
• Claudia Breindl · Hersbruck, DE
• Harald Trauthwein · Munich, DE
• Elisabeth Eichberger · Passau, DE
• Anton Eichberger · Passau, DE

Key dates

• Filing date: Jul 3, 2000
• Grant date: Apr 24, 2001
• Expiry date: Jul 3, 2020

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07C209/60
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

Process for the preparation of an N-arylethylaniline of the formula (I) EQU Ar--N(R.sup.1).sub.2-n (CHR.sup.2 CHR.sup.3 Ar').sub.n (I) by reacting an aromatic olefin of the formula (II) EQU Ar'CR.sup.3 =CHR.sup.2 (II) with an aniline of the formula (III) EQU Ar--N(R.sup.1).sub.2-n (H).sub.n (III) in an inert solvent in the presence of at least one basic catalyst selected from the group consisting of alkali metal alcoholates and alkaline earth metal alcoholates or alkali metal amides and alkaline earth metal amides, where, in the formulae (I) to (III), PA1 Ar and Ar', independently of one another, are an aryl radical selected from the group consisting of the fused and nonfused C.sub.6 -C.sub.22 -aromatics and of the fused or nonfused C.sub.5 -C.sub.22 heteroaromatics which have at least one nitrogen, oxygen or sulfur atom in the ring; PA1 R.sub.1, R.sub.2 and R.sub.3, independently of one another, are a hydrogen atom, a C.sub.1 -C.sub.8 -alkyl radical or an aryl radical Ar; and PA1 n is the number 1 or 2.