1-Methylpyrrole → 1-Methyl-4-(1-methylpyrrol-2-yl)-4-piperidinol

Participants

Reaction Conditions

Reaction Steps

A 1.6 M solution of n-butyllithium in hexane (175 ml) was added dropwise at room temperature to a solution of 24.2 g of N-methylpyrrole in 250 ml of diethyl ether contained in a reaction flask (under a nitrogen blanket). After addition was completed, the resulting mixture was heated at reflux with stirring for 16 hours, then cooled to 0° C. 34 Grams of 1-methyl-4-piperidone was added dropwise from a dropping funnel with the temperature maintained at 0° C. during the addition by cooling the reaction flask with dry ice-acetone bath. The reaction mixture was stirred at room temperature for 3 hours, and then quenched in ice water to yield 26 g of the title compound in a crystalline form; recrystallization from heptane gave white prisms, m.p. 123°-123.5°.

Provenance & Evidence