1-Methylpiperazine → 1-(5-Bromo-1,3-thiazol-2-yl)-4-methylpiperazine

Participants

Reaction Conditions

Reaction Steps

A solution of 2,5-dibromothiazole (1.000 g, 4.116 mmol) in DIPEA (3.00 mL) was charged with 1-methylpiperazine (0.457 mL, 4.12 mmol) and heated to 110° C. for 3 h then an additional 48 h at rt. The reaction mixture was partitioned between CHCl3 and H2O, and the layers were separated. The aqueous layer was re-extracted with CHCl3 (3×) and the combined organic fractions were dried over Na2SO4, filtered and concentrated in vacuo. The crude material was purified by chromatography on silica gel [eluting with 5% EtOAc in CHCl3→20% EtOAc in CHCl3] resulting in the title compound as an off-white solid. 1H NMR (400 MHz, CDCl3): δ=2.34 (s, 3H), 2.48-2.56 (m, 4H), 3.42-3.51 (m, 4H), 7.07 (s, 1H). MS (ES+): m/z=262.09/264.06 (51/49) [MH+]. HPLC: tR=1.57 & 0.53 min (peak splitting; ZQ2, polar—5 min).

Provenance & Evidence