4-Methylmorpholine → 4-[4-(chloromethyl)-1,3-thiazol-2-yl]-N-(4-pentylbenzyl)benzamide

Participants

Reaction Conditions

Reaction Steps

N-methylmorpholine (1.7 mL, 15.3 mmol) and isobutyl chloroformate (1.0 mL, 7.65 mmol) were added to a solution of 4-[4-(chloromethyl)-1,3-thiazol-2-yl]benzoic acid (1.85 g, 7.29 mmol) in anhydrous THF (30 mL) at 0° C. The reaction mixture was stirred at 0° C. for 30 min, then (4-pentylbenzyl)amine hydrochloride (1.64 g, 7.65 mmol) was added neat. The reaction mixture was stirred for 15 min at 0° C., then 2 hours at RT. The reaction mixture was diluted with DCM (100 mL) and washed with 1M aqueous HCl (50 mL), then saturated aqueous NaHCO3 (50 mL). The aqueous layers were extracted with DCM (100 mL). The combined organic layers were dried over MgSO4 and the solvents were removed under reduced pressure to give a brown solid. Recrystallization from a mixture MeOH/water gave 2.30 g (75%) of the title compound as beige solid. HPLC, Rt: 5.2 min (purity: 98.0%). 1H NMR (CDCl3) δ: 8.01 (d, J=8.3 Hz, 2H), 7.86 (d, J=8.3 Hz, 2H), 7.37 (s, 1H), 7.30 (d, J=8.0 Hz, 2H), 7.19 (d, J=8.0 Hz, 2H), 6.47 (m, 1H), 4.76 (s, 2H), 4.63 (d, J=5.5 Hz, 2H), 2.61 (t, J=7.7 Hz, 2H), 1.63 (m, 2H), 1.34 (m, 4H), 0.90 (t, J=6.8 Hz, 3H).

Provenance & Evidence