1-Indanone → 1-(2-(Indan-1-yl)ethyl)-4-(3,4-dimethoxyphenyl)piperidine

Participants

Reaction Steps

A suspension of 0.6 g of lithium aluminium hydride in 35 ml of THF is treated dropwise with stirring under inert reaction conditions with a solution of 6.3 g of 1-(indan-1-ylacetyl)-4-(3,4-dimethoxyphenyl)piperidine [obtainable by reaction of 1-indanone with diethylethoxycarbonyl methanephosphonate, subsequent hydrogenation with H2 /Pd-C, conversion of the ester present to an acid chloride and amide formation with 4-(3,4-dimethoxyphenyl)piperidine] in 70 ml of THF and the mixture is boiled for 2 hours. A further 0.8 g of lithium aluminium hydride is then added and the mixture is refluxed for a further 3 hours. The reaction mixture is then treated with methanol and subsequently with water and worked up in the customary manner. Chromatography (methyl tertbutyl ether/petroleum ether/diethylamine) gives 1-(2-(indan-1-yl)ethyl)-4-(3,4-dimethoxyphenyl)piperidine.

Provenance & Evidence