Tetrahydrofuran → (1-Methyl-4-piperidinyl)[3-[2-(3-fluorophenyl)ethyl]-2-pyridinyl]methanone

Participants

Reaction Steps

To a solution of 3-[2-(3-fluorophenyl)ethyl]-2pyridine carbonitrile (28.0 o, 0.123 mole) in 150 mL of dry THF is added 92 mL (1.48 moles/liter, 0.136 mole) of N-methylpiperidyl magnesium chloride over 10 minutes maintaining the temperature at 45°-50° C. The reaction is maintained at 40° C. to 50° C. for another 10 minutes and at ambient temperature for 45 minutes. The reaction is quenched to below pH 2 with aqueous hydrochloric acid and the resulting solution is stirred at 25° C. for 1 hour. The pH of the solution is adjusted to about 8, the oroduct is extracted with ethyl acetate, and the solution is concentrated to a residue. Following purification by silica gel chromatography, 38.3 g of product is obtained as a brown oil.

Provenance & Evidence