Sodium Acetate → HCID 13336358, compound

Participants

Reaction Steps

N-Ethyl-N-[(1-benzylpiperidin-4-yl)-methyl]-2-phenylquinoline-4-carboxamide (9.6 g) is heated in ethanol (200 ml) until it has dissolved. After cooling, this solution is treated with a 4.5N ethanolic solution of hydrogen chloride (9.2 ml), 10% strength palladium-on-charcoal (2.9 g) as a catalyst and, finally, sodium acetate (1.7 g). The mixture is hydrogenated at 60° C., with stirring, under a hydrogen pressure equal to normal pressure (1 bar), for 5 hours. After 5 hours (at which time the amount of hydrogen absorbed is 470 ml), the catalyst is removed by filtration, the ethanol is evaporated off by distillation under reduced pressure, the residue is taken up in water (200 ml) and the mixture is brought to pH 10 by the addition of a concentrated solution of sodium hydroxide and extracted with ether (3×100 ml). The organic phase is washed with water (3×50 ml), dried over magnesium sulphate and evaporated under reduced pressure. N-ethyl-N-[(piperidin-4-yl)methyl]-2-phenylquinoline-4-carboxamide (5 g) is isolated in this way; it is dissolved in acetone and converted to the monohydrochloride by the addition of a solution of hydrogen chloride in ether. This monohydrochloride melts at 219° C.

Provenance & Evidence