Diethyl Ether → 2-methyl-3-(2-ethyl N-morpholinyl)indene

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Reaction Steps

5.8 g (0.05 mol) indene was taken up in 50 mL dry ether under nitrogen. To this solution a solution of 2.303 g (0.05 mol) n-butyllithium (2.1 M) in 150 mL of ether was added dropwise. The solution was stirred at room temperature for 2 hours and a solution of 33.5 g (0.18 mol) N-(2-chloroethyl)morpholine was added and stirred overnight at room temperature. The reaction mixture was neutralized with saturated ammonium chloride solution and the ether layer separated and dried over magnesium sulfate and concentrated in vacuo giving a yellow oil. The product was redissolved in ether and extracted with 200 ml 2 N HCl twice. The aqueous layer was again extracted with ether and cooled in an ice bath. This cooled, acidic mixture was then slowly neutralized with 35% NaOH and extracted twice with ether. The organic layers were pooled and washed with water, saturated NaCl and dried over magnesium sulfate to give 6.9 g (60%) of the desired 3-[2-(4-morpholinyl)ethyl]indene (Formula II R2 =R3 =R4 =hydrogen; Alk=1,2-ethylene).

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