L-Tartaric acid → [(4-chloro-thiazol-5-yl)methyl]-isobutyl-piperidin-4-yl-amine L-tartrate

Participants

Reaction Steps

Add L-tartaric acid (8.08 g, 53.8 mmol) to absolute ethanol (300 mL) and heat until the L-tartaric acid goes into solution. Add this warm solution of L-tartaric acid to [(4-chloro-thiazol-5-yl)methyl]-isobutyl-piperidin-4-yl-amine (15.50 g, 53.9 mmol) in absolute ethanol (200 mL) at room temperature. Stir for 18 hours under nitrogen at room temperature. Cool the reaction to 0° C. and filter off the solid. Wash the solid with cold absolute ethanol and dry in a vacuum oven at 50° C. to yield 22.16 g (94%) of [(4-chloro-thiazol-5-yl)methyl]-isobutyl-piperidin-4-yl-amine L-tartrate: mass spectrum (ion spray): m/z=288.1 (M+1); 1H NMR (CDCl3): δ=8.91 (s, 1H), 4.44 (s, 2H), 3.89 (s, 2H), 3.50-3.47 (m, 2H), 3.01-2.93 (m, 2H), 2.89-2.81 (m, 1H), 2.37 (d, 2H), 2.03-2.00 (m, 2H), 1.87-1.70 (m, 3H), 0.94 (d, 6H); LC/MS (90/5/5 to 0/95/5 water/acetonitrile/5% formic acid in water) XTerra MS C18 2.1 mm×50 mm×3.5 micron: Rt 0.96 minutes, Purity: 100%.

Provenance & Evidence