Dimethylformamide → 8-(2-Quinolinyl)-1,4-dioxa-8-azaspiro[4.5]decane

Participants

Reaction Steps

A mixture of 10 g (0.0613) of 2-chloroquinoline, 27 g (0.1886 mol) of 1,4-dioxa-8-azaspiro[4.5]decane, 13 g (0.0941) of K2CO3, and 75 ml of dimethylformamide is stirred at 100°-110° C. for 4 days. The reaction mixture is allowed to cool to ambient temperature, diluted with water and extracted with ethyl acetate. The combined organic extracts are washed copiously with water, then brine, dried over Na2SO4, and concentrated in vacuo to give a waxy solid. Trituration with ether furnishes 3.6 g (22%) of title compound: IR (KBr) 1620, 1610, and 1510 cm-1 ; NMR (CDCl3) δ 7.92 (d, 1H), 7.78-7.50 (m, 3H), 7.30-7.22 (m, 1H), 7.04 (d, 1H), 4.02 (s, 4H), 3.94-3.86 (m, 4H), and 1.88-1.76 (m, 4H).

Provenance & Evidence