4-Nitrophenethyl bromide → 1,3-dihydro-1-oxo-1'-[2-(4-nitrophenyl)-1-ethyl]-spiro[2H-indene-2,4'-piperidine]

Participants

Reaction Steps

A mixture of 0.60 g (3.0 moles) 1,3-dihydro-1-oxospiro[2H-indene-2,4'-piperidine], 0.71 g (3.1 mmoles) 4-nitrophenethyl bromide, and 0.28 g (3.3 mmoles) sodium bicarbonate in 3 ml ethanol was heated at reflux for 6 hours. The solvent was removed in vacuo and the residue was partitioned between 20 ml ethyl acetate and 5 ml dilute bicarbonate solution. The layers were separated and the aqueous layer was extracted with 20 ml ethyl acetate. The combined extract was washed wth 5 ml water and brine, dried, and the solvent was removed in vacuo to give 1.08 g crude product as a gum. This was purified by flash chromatography on silica gel eluting with methanol:chloroform (2:98). The material obtained was crystallized from 1:10 methylene chloride:ether to give 0.61 g (58%) product, m.p. 187°-188° C.

Provenance & Evidence