Phase transfer catalytic process for preparing intermediates of

Details Phase transfer catalytic process for preparing intermediates of Phase transfer catalytic process for preparing intermediates of

1993-08-18

1994-03-01

Evans, Joseph E.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

568649, C07D30128, C07D30323, C07C 4103, C07C 43205

Patent

active

052909581

ABSTRACT:
A phase transfer catalytic process for the preparation of epoxide and halohydrin intermediates, which can be subsequently and directly reacted with isopropylamine to produce beta-adrenergic antagonists such as atenolol, propanolol and their derivatives. In the process disclosed in the present invention, quaternary ammonium salts of high alkyl groups or tertiary ammonium salts of lower alkyl groups are used as catalyst in the phase transfer catalytic oxygenated-alkylation reaction between an aromatic alcohol such as p-hydroxyphenyl acetamide (for the production of atenolol) or .alpha.-naphthol (for the production of propranolol) and epichlorohydrin to yield epoxide and halohydrin intermediates. The quaternary ammonium salts of high alkyl groups are represented by the following formula: ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, and R.sub.4 are C.sub.1 to C.sub.20 alkyl groups and at least one of the R.sub.1, R.sub.2, R.sub.3, or R.sub.4 is a C.sub.9 to C.sub.20 alkyl group, and X is a halide group. And the tertiary ammonium salts of lower alkyl groups are presented by the following formula: ##STR2## wherein R.sub.5 is a C.sub.1 to C.sub.20 alkyl group, H is hydrogen, and X is a halide group.

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