Fumaric Acid → 5-(4-Chlorophenyl)-3-(1-methyl-2-pyrrolidinyl)pyridine fumarate

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Reaction Steps

The above-referenced pyridine was converted into invention compound of Formula I by the addition of one equivalent of fumaric acid to a methanol (15 mL) solution of the free amine at 25° C. After 30 minutes the solvent was removed in vacuo and the residue pumped under high vacuum. Trituration with diethyl ether followed by recrystallization from ethyl acetate afforded 5-(4-chlorophenyl)-3-(1-methyl-2-pyrrolidinyl)pyridine fumarate, (72%) as a colorless solid. M.p. 159°-160° C. (EtOAc); 1H NMR (DMSO-d6, 300 MHz): 6 8.84 (d, J=3 Hz, 1 H), 8.58 (d, J=3 Hz, 1 H), 8.08 (t, J=2 Hz, 1 H), 7.79 (d, J=8 Hz, 2 H), 7.56 (d, J=8 Hz, 2 H), 6.62 (s, 2 H), 3.49 (t, J=6 Hz, 1 H), 3.32 (m, 1 H), 2.52 (m, 1 H), 2.28 (m, 1 H), 2.24 (s, 3 H), 1.9 (m, 3 H).

Provenance & Evidence