Sodium Hydroxide → HCID 44514740, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 10 g of 5-bromo-3-{[(2R)-1-methylpyrrolidin-2-yl]methyl}-1H-indole (as oil containing traces of toluene, HPLC purity 98.3%) in 20 ml, of isopropanol, were dropped in about 2 hours at 30-35° C. into a solution composed of 65 ml, of isopropanol, 15 mL of water and 4.4 g of anhydrous fumaric acid. After stirring for 2 hours at 20-25° C. the reaction mixture was filtered and the crystalline product dried at 80° C. obtaining 7.12 g (Karl Fischer 0.08%, HPLC purity 99.4%). By cooling the mother liquors at −15° C., 1.23 g (Karl Fischer 0.17%, HPLC purity 99.0%) were further obtained. The product (molecule 7 fumarate) has a 199.4° C. (DSC 10°/min) melting point, 1H-NMR (DMSO-d6) spectrum: δ 11.18 (br s, 1H), 7.75 (d, j=1.9 Hz, 1H), 7.3 (d, j=8.6 Hz, 1H) 7.3 (d, j=2.3 Hz, 1H), 7.18 (dd, j=1.9 Hz and 8.6 Hz, 1H), 6.54 (s, 2H), 3.41-3.31 (m, 1H), 3.21 (dd, j=14 Hz and 4.5 Hz, 1H), 3.13-3.02 (m, 1H), 2.8-2.65 (m, 2H), 2.62 (s, 3H), 1.92-1.72 (m, 3H), 1.70-1.56 (m, 1H) and a titre with NaOH corresponding to a 1:1 stoichiometry with fumaric acid.

Provenance & Evidence