Tetrahydrofuran → HCID 12859835, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of 73.1 g (0.489 mol) 3-(diethylamino)-propyl chloride and 11.87 g (0.489 mol) of magnesium in 300 mL of tetrahydrofuran is initiated with 0.25 mL of 3M ethylmagnesium bromide in diethyl ether and is refluxed overnight. After this time, the reaction is allowed to cool to 40° C. and is treated with 29.6 g (0.245 mol) of 4-fluorobenzonitrile. The initial exotherm is followed by applied heat and the reaction is refluxed for 3 hr. After this time, the reaction is allowd to cool to room temperature and is quenched with 250 mL of water. This mixture is extracted with 2×250 mL of methylene chloride. The combined organic layers are acidifed to pH=1 with 2N aq. hydrochloric acid and the resulting layers separated. The aqueous extract is washed with 100 mL of methylene chloride and is made basic with 4N of sodium hydroxide. The aqueous mixture is extracted with 3×300 mL of methylene chloride. The combined organic layers are dried over sodium sulfate, filtered and the solvent distilled in vacuo to provide crude title compound. This liquid is distilled under vacuum to provide the title compound.

Provenance & Evidence