Dichloromethane → Morpholinium, 4-(chloromethylene)-, chloride

Participants

Reaction Conditions

Reaction Steps

Under dry nitrogen, N-formyl piperidine (124 gm, 1.10 mol), rapidly stirring at -4° C., is treated dropwise over the course of 30 minutes with thionyl chloride (144 gm, 1.21 mol), the temperature being maintained below 0° C. with ice-methanol cooling. The resulting solution is warmed slowly to 56° C. over 80 minutes with the application of vacuum (at about 30 mm). A mixture of methylene chloride 10 ml and toluene (40 ml) is added, and the resulting slurry is concentrated to dryness (37° C., about 30 mm vacuum). This stripping procedure is repeated, and final concentration is accomplished by the application of higher (about 5 mm) vacuum (30°-42° C., 30 min), to yield solid N-(chloromethylene)-morpholinium chloride.

Provenance & Evidence