Hydrochloric Acid → 8-(1-Pyrrolidinyl)-1,4-dioxaspiro[4.5]decane-8-carbonitrile

Participants

Reaction Steps

Pyrrolidine (22.5 ml, 0.306 mol), cyclohexane-1,4-dione monoethylene ketal (10.0 g, 0.064 mol) and potassium cyanide (10.0 g, 0.15 mol) was added to a mixture of 4 N hydrochloric acid (17 ml) and methanol (10 ml), while cooling with ice. The mixture was stirred at room temperature for 74 h and then, after addition of water (80 ml), extracted with diethyl ether (4×70 ml). After concentration, the residue was taken up in methylene chloride (70 ml) and the mixture was dried with magnesium sulfate overnight. The organic phase was concentrated and 8-pyrrolidin-1-yl-1,4-dioxaspiro[4.5]decane-8-carbonitrile was obtained as a white solid with a melting point of 65-67° C. in a yield of 68% (10.2 g).

Provenance & Evidence