Optically active aryloxypropanolamines and arylethanolamines

US4990668A · kind A · utility

Assignee

• E.I. DU PONT DE NEMOURS AND COMPANY · US

Inventors

• Khuong H. X. Mai · Vernon Hills, US
• Ghanshyam Patil · McKeesport, US
• William L. Matier · Libertyville, US

Key dates

• Filing date: Dec 4, 1985
• Grant date: Feb 5, 1991
• Expiry date: Dec 4, 2005

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D493/04
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

Described is a process for preparing a racemic or chiral aryloxypropanolamine (1) or arylethanolamine (2) of the formula ##STR1## wherein Ar is aryl, substituted aryl, heteroaryl, or aralkyl and R is alkyl, substituted alkyl, aralkyl, or WB wherein W is a straight or branched chain alkylene of from 1 to about 6 carbon atoms and wherein B is --NR.sub.2 COR.sub.3, --NR.sub.2 CONR.sub.3 R.sub.4, --NR.sub.2 SO.sub.2 R.sub.3, --NR.sub.2 SO.sub.2 NR.sub.3 R.sub.4, or --NR.sub.2 COOR.sub.5, where R.sub.2, R.sub.3, R.sub.4, and R.sub.5 may be the same or different and may be hydrogen, alkyl, alkoxyalkyl, alkoxyaryl, cycloalkyl, alkenyl, alkynyl, aryl, heteroaryl, or aralkyl, except that R.sub.3 and R.sub.5 are not hydrogen when B is --NR.sub.2 SO.sub.2 R.sub.3 or --NR.sub.3 COOR.sub.5, or R.sub.3 and R.sub.4 may together with N form a 5- to 7-membered heterocyclic group. The process can be used to prepare beta-blocking agents, useful in the treatment of cardiac conditions.