Reaction #1128

Reaction equation

pyridine

5-(4-fluorophenyl)-3-(1-methyl-2-pyrrolidinyl) pyridine

fumaric acid

→

5-(4-fluorophenyl)-3-(1-methyl-2-pyrrolidinyl)pyridine fumarate

Yield 63.0%

Solvents

methanol

Conditions

Workup

1. 1
   OtherAfter 30 minutes the solvent was removed in vacuo
2. 2
   OtherTrituration with diethyl ether followed by recrystallization from ethyl acetate

Procedure

The pyridine derivative described above was converted to a compound of the invention having 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-fluorophenyl)-3-(1-methyl-2-pyrrolidinyl)pyridine fumarate, (63%). M.p. 159°-160° C. (EtOAc); 1H NMR (D2O, 300 MHz): δ 8.87 (s, 1 H), 8.68 (s, 1 H), 8.26 (s, 1 H), 7.73 (dd, J=8, 6 Hz, 2 H), 7.30 (app. t, J=8 Hz, 2 H), 6.61 (s, H), 4.56 (bm, 1 H), 3.91 (bm, 1 H), 3.41 (bm, 1 H), 2.83 (s, 3 H), 2.67 (m, 1 H), 2.3-2.5 (m, 3 H).

Source