Preparation of N-substituted pyrrolidin-2-ones

US5101044A · kind A · utility

Assignee

• BASF SE

Inventors

• Ludwig Schuster · Schifferstadt, DE
• Ulrich Koehler · Heidelberg, DE

Key dates

• Filing date: Sep 4, 1990
• Grant date: Mar 31, 1992
• Expiry date: Sep 4, 2010

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D207/38
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

A process for the preparation of N-substituted pyrrolidin-2-ones of the general formula I ##STR1## where R.sup.1 is C.sub.1 - to C.sub.20 -alkyl, C.sub.6 - to C.sub.10 aryl or C.sub.7 - to C.sub.12 -aralkyl comprises hydrogenolytically cleaving 5-iminopyrrolidin-2-ones of the general formula II ##STR2## in which the R.sup.1 radicals are identical or different C.sub.1 - to C.sub.20 -alkyl, C.sub.6 - to C.sub.10 -aryl or C.sub.7 - to C.sub.12 -aralkyl, at super-atmospheric pressure and elevated temperature in the presence of a hydrogenation catalyst to give the pyrrolidin-2-ones I; specifically, the 5-iminopyrrolidin-2-ones of the formula II are obtained by reacting .beta.-cyanopropionic acid esters of the general formula III ##STR3## where R.sup.2 is C.sub.1 - to C.sub.20 -alkyl, C.sub.7 - to C.sub.12 -aralkyl or C.sub.6 - to C.sub.10 -aryl, with an amine of the general formula IV EQU R.sup.1 --NH.sub.2 IV where R.sup.1 is as defined above.