Tert-butyl 4-(3-acetyl-7-methoxynaphthalen-1-yl)piperazine-1-carboxylate → (E)-tert-butyl 4-(3-(3-(dimethylamino)acryloyl)-7-methoxynaphthalen-1-yl)piperazine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

tert-butyl 4-(3-acetyl-7-methoxynaphthalen-1-yl)piperazine-1-carboxylate (107) (1.5 g) and N,N-dimethylformamide dimethylacetal were charged in a flask and heated at 100° C. for 36 hours. More N,N-dimethylformamide dimethylacetal (10 ml) was added to the reaction, the temperature was raised to 120° C. and the reaction was allowed to proceed overnight. The reaction was cooled and poured onto water. The solid was extracted with ethyl acetate (2×100 ml), the organics combined, washed with water (1×100 ml) and brine (1×100 ml), dried over sodium sulfate and concentrated. Column chromatography (100% ethyl acetate) gave (E)-tert-butyl 4-(3-(3-(dimethylamino)acryloyl)-7-methoxynaphthalen-1-yl)piperazine-1-carboxylate (108) as a light yellow foam (1.59 g) LCMS (m/z): 440 [M+H].

Provenance & Evidence