Process for preparing aminoalkylpyrrolobenzoxazalkanes

Claim 1

A process for the preparation of an aminoalkylpyrrolobenzoxazalkane of the formula ##STR3## wherein Y is hydrogen, halogen, lower alkoxy, lower alkyl, trifluoromethyl, nitro or amino; R 1 is hydrogen or lower alkyl; R 2 is hydrogen, alkyl of from 1 to 5 carbon atoms, phenyl, cycloalkyl of from 3 to 6 carbon atoms, phenalkyl of the formula C 6 H 5 (CH 2 ) n --, or cycloalkylalkyl of from 4 to 7 carbon atoms; R 3 is alkyl of from 1 to 5 carbon atoms, phenyl, cycloalkyl of from 3 to 6 carbon atoms, phenylalkyl of the formula C 6 H 5 (CH 2 ) n -- or cycloalkylalkyl of from 4 to 7 carbon atoms; m is the integer 1 or 2 and n is the integer 1, 2 or 3; which comprises reacting an orthofluorophenylalkylpyrrole of the formula ##STR4## with a halogenated acetonitrile in the presence of an organic solvent which is inert under the reaction conditions at a cooled temperature and introducing hydrogen chloride gas into the reaction solution forming a ketimine; hydrolyzing said ketimine to produce a haloketone of the formula ##STR5## wherein X is chlorine or bromine; reacting said haloketone with an amine of the formula H 2 NR 2 R 3 at a temperature of from ambient to 150° C. in the presence of an acid scavenger to produce a pyrrylamino ketone of the formula ##STR6## reducing said pyrrylamino ketone to a pyrrylamino ethanol of the formula ##STR7## and reacting said pyrrylamino ethanol with a mineral base to effect condensation to said aminoalkylpyrrolobenzoxazalkane.