Benzene → 4-(3,6-Dihydro-4-(1-pyrrolidinyl)-1(2H)-pyridinyl]benzonitrile

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Reaction Steps

A solution of 24 g (0.1199 mol) of the compound of (b), 15 ml (12.78 g/0.1796 mol) of pyrrolidone, 240 mg of p-toluenesulfonic acid, and 100 ml of benzene is stirred at reflux with the azeotropic removal of water for 6 hours. After cooling, the resulting precipitate is collected and triturated with ethyl ether to afford 20 g (66%) of title compound: m.p. 126°-129° C.; IR (KBr) 2200, 1635, and 1600 cm-1 ; 'H NMR (CDCl3) δ 7.48 (d, 2H), 6.7 (d, 2H), 4.3-4.1 (m, 1H), 3.95-3.45 (m, 4H), 3.2-2.85 (m, 4H), 2.65-2.25 (m, 2H), and 1.95-1.75 (m, 4H).

Provenance & Evidence