Dichloromethane → 3,4-Dihydro-9-(4,4-diphenylbutylamino)acridin-1(2H)-one

Participants

Reaction Conditions

Reaction Steps

In a mixture consisting of 480 ml of dichloromethane and 320 ml of 50% NaOH were combined 8.00g of 9-amino-3,4-dihydroacridin-1(2H)-one, 68 g (6 eq) of 1-mesyloxy-4,4-diphenylbutane and 2.56 g (0.20 eq) of tetrabutylammonium hydrogensulfate used as a phase transfer catalyst. The biphasic mixture was jacket cooled to 3° C. and was then mechanically stirred for 3 days. As no further reaction occurred, the reaction mixture was diluted with water and the organic phase was separated. Analysis by thin layer chromatography indicated a 1:1 mixture of the end product and the starting material. The dichloromethane layer was evaporated to a gum. The gum was diluted with dichloromethane and mixed with 1:1 alumina/sand to immobilize it as a solid for Soxhlet extraction. The dichloromethane was evaporated and the solid was put into a Soxhlet extraction thimble and extracted with hexane for 4 hours. Since no further extraction occurred after 4 hours, the hexane solution was evaporated to an oil. The oil was chromatographed over silica gel (EtOAc) and the resultant solid rechromatographed through alumina (Et2O) to yield a solid. The solid was recrystallized from Et2O/hexanes to yield 1.22 g (8%) of product, melting point 86°-88° C.

Provenance & Evidence