N,N-Dimethylaniline → HCID 14405683, compound

Participants

Reaction Conditions

Reaction Steps

4.4 g (20 mmol) of 1-benzyl-4-piperidinecarboxylic acid are added to 12 ml (165 mmol) of thionyl chloride, and the mixture is stirred under an inert atmosphere. Stirring is maintained for 16 h at 20° C., and the excess thionyl chloride is then evaporated off under reduced pressure. The residue is taken up with 25 ml of toluene and the mixture again evaporated under reduced pressure. The solid residue is dissolved in dichloromethane, and 5.7 ml (45 mmol) of N,N-dimethylaniline and 3.4 g (20 mmol) of 1,2,3,4-tetrahydrobenzofuro[2,3-c]pyridine (base), dissolved in 12 ml of dichloromethane, are added under argon. The mixture is stirred for 2 h at 20° C. and then poured into water. The insoluble material is isolated by filtration, washed with water and suspended in a mixture of water and ethyl acetate. This suspension is treated with ammonia solution, and the organic phase is separated off after settling has taken place, washed with water and dried. The solvent is evaporated off under reduced pressure and the amide thereby obtained dried under vacuum. The hydrochloride of the latter is prepared in 0.1N hydrochloric acid in isopropyl alcohol, and recrystallized in ethanol.

Provenance & Evidence