Trifluoroacetic acid → HCID 57640346, compound

Participants

Reaction Steps

To a cooled (0° C.) solution of 4-{isobutyl-[(thiazol-4-yl)methyl]-amino}-piperidine-1-carboxylic acid tert-butyl ester (540 mg, 1.53 mmol, 1 eq.) in anhydrous dichloromethane (3 ml), is added anisole (2.5 g, 23 mmol, 15 eq.) and trifluoroacetic acid (2.6 g, 23 mmol, 15 eq.). The reaction is allowed to warm to room temperature and stirred for 4-5 hours. The reaction mixture is loaded on a SCX-2 column. The column is first washed with methanol and then the base eluted with 20% 2N NH3 in methanol in dichloromethane. The solvents are removed in vacuo to afford isobutyl-(piperidin-4-yl)-[(thiazol-4-yl)methyl]-amine (387 mg). m/z=254 (M+1); 1H NMR (CDCl3): δ=8.27 (1H, d), 7.22-7.21 (1H, m), 3.86 (2H, d), 3.15 (2H, brd), 2.62-2.49 (3H, m), 2.30 (2H, d), 2.03 (1H, brs), 1.78 (2H, d), 1.66-1.59 (1H, m), 1.50-1.40 (2H, m), 0.86 (6H, d).

Provenance & Evidence