Acrylamide → 4-(5H-dibenzo[a,d]cyclohepten-5-yl)-1-(2-carbamoylethyl)piperidine

Participants

Reaction Steps

1.00 gram (3.62 millimoles) of 4-(5H-dibenzo-[a,d]cyclohepten-5-yl)piperidine, 0.26 gram (3.62 millimoles) of acrylamide, 0.04 gram (0.36 millimole) of triethylamine and 20 milliliters of isopropyl alcohol were stirred together at reflux temperature while protected from atmospheric moisture. A TLC analysis of a sample of the reaction mixture indicated presence of some piperidine compound but no acrylamide. 50 milligrams (0.7 millimole) of acrylamide in 1 milliliter of isopropyl alcohol was added and the reaction continued at reflux temperature for a total of about 3.5 hours. The reaction mixture was allowed to cool to room temperature and the solvent then removed in vacuo to obtain the desired 4-(5H-dibenzo[a,d]cyclohepten-5-yl)-1-(2-carbamoylethyl)piperidine product as residue. The crude product was crystallized from methylene chloride/hexane, then dried in vacuo overnight at 100° C. to obtain 900 milligrams (72 percent yield) of product, m.p. 135°-140° C.

Provenance & Evidence